diff --git a/.circleci/config.pkl b/.circleci/config.pkl
index ae3cfd16..5446405c 100644
--- a/.circleci/config.pkl
+++ b/.circleci/config.pkl
@@ -14,7 +14,7 @@
 // limitations under the License.
 //===----------------------------------------------------------------------===// 
 // File gets rendered to .circleci/config.yml via git hook.
-amends "package://pkg.pkl-lang.org/pkl-project-commons/pkl.impl.circleci@1.1.0#/PklCI.pkl"
+amends "package://pkg.pkl-lang.org/pkl-project-commons/pkl.impl.circleci@1.1.1#/PklCI.pkl"
 
 import "jobs/BuildNativeJob.pkl"
 import "jobs/GradleCheckJob.pkl"
@@ -96,6 +96,11 @@ local buildNativeJobs: Mapping<String, BuildNativeJob> = new {
       musl = true
       isRelease = _dist == "release"
     }
+    ["pkl-cli-windows-amd64-\(_dist)"] {
+      arch = "amd64"
+      os = "windows"
+      isRelease = _dist == "release"
+    }
   }
 }
 
@@ -108,6 +113,11 @@ local gradleCheckJobs: Mapping<String, GradleCheckJob> = new {
     javaVersion = "21.0"
     isRelease = false
   }
+  ["gradle-check-jdk17-windows"] {
+    javaVersion = "17.0"
+    isRelease = false
+    os = "windows"
+  }
 }
 
 jobs {
diff --git a/.circleci/config.yml b/.circleci/config.yml
index 0ddc93f9..021ae3cb 100644
--- a/.circleci/config.yml
+++ b/.circleci/config.yml
@@ -12,18 +12,12 @@ jobs:
     - run:
         command: |-
           export PATH=~/staticdeps/bin:$PATH
-          ./gradlew --info --stacktrace -DreleaseBuild=true pkl-cli:macExecutableAmd64 pkl-core:testMacExecutableAmd64
+          ./gradlew --info --stacktrace -DtestReportsDir=${HOME}/test-results -DreleaseBuild=true pkl-cli:macExecutableAmd64 pkl-core:testMacExecutableAmd64
         name: gradle buildNative
     - persist_to_workspace:
         root: '.'
         paths:
         - pkl-cli/build/executable/
-    - run:
-        command: |-
-          mkdir ~/test-results/
-          find . -type f -regex ".*/build/test-results/.*xml" -exec cp {} ~/test-results/ \;
-        name: Gather test results
-        when: always
     - store_test_results:
         path: ~/test-results
     environment:
@@ -94,18 +88,12 @@ jobs:
     - run:
         command: |-
           export PATH=~/staticdeps/bin:$PATH
-          ./gradlew --info --stacktrace -DreleaseBuild=true pkl-cli:linuxExecutableAmd64 pkl-core:testLinuxExecutableAmd64
+          ./gradlew --info --stacktrace -DtestReportsDir=${HOME}/test-results -DreleaseBuild=true pkl-cli:linuxExecutableAmd64 pkl-core:testLinuxExecutableAmd64
         name: gradle buildNative
     - persist_to_workspace:
         root: '.'
         paths:
         - pkl-cli/build/executable/
-    - run:
-        command: |-
-          mkdir ~/test-results/
-          find . -type f -regex ".*/build/test-results/.*xml" -exec cp {} ~/test-results/ \;
-        name: Gather test results
-        when: always
     - store_test_results:
         path: ~/test-results
     environment:
@@ -120,18 +108,12 @@ jobs:
     - run:
         command: |-
           export PATH=~/staticdeps/bin:$PATH
-          ./gradlew --info --stacktrace -DreleaseBuild=true pkl-cli:macExecutableAarch64 pkl-core:testMacExecutableAarch64
+          ./gradlew --info --stacktrace -DtestReportsDir=${HOME}/test-results -DreleaseBuild=true pkl-cli:macExecutableAarch64 pkl-core:testMacExecutableAarch64
         name: gradle buildNative
     - persist_to_workspace:
         root: '.'
         paths:
         - pkl-cli/build/executable/
-    - run:
-        command: |-
-          mkdir ~/test-results/
-          find . -type f -regex ".*/build/test-results/.*xml" -exec cp {} ~/test-results/ \;
-        name: Gather test results
-        when: always
     - store_test_results:
         path: ~/test-results
     environment:
@@ -186,18 +168,12 @@ jobs:
     - run:
         command: |-
           export PATH=~/staticdeps/bin:$PATH
-          ./gradlew --info --stacktrace -DreleaseBuild=true pkl-cli:linuxExecutableAarch64 pkl-core:testLinuxExecutableAarch64
+          ./gradlew --info --stacktrace -DtestReportsDir=${HOME}/test-results -DreleaseBuild=true pkl-cli:linuxExecutableAarch64 pkl-core:testLinuxExecutableAarch64
         name: gradle buildNative
     - persist_to_workspace:
         root: '.'
         paths:
         - pkl-cli/build/executable/
-    - run:
-        command: |-
-          mkdir ~/test-results/
-          find . -type f -regex ".*/build/test-results/.*xml" -exec cp {} ~/test-results/ \;
-        name: Gather test results
-        when: always
     - store_test_results:
         path: ~/test-results
     environment:
@@ -269,18 +245,12 @@ jobs:
     - run:
         command: |-
           export PATH=~/staticdeps/bin:$PATH
-          ./gradlew --info --stacktrace -DreleaseBuild=true pkl-cli:alpineExecutableAmd64 pkl-core:testAlpineExecutableAmd64
+          ./gradlew --info --stacktrace -DtestReportsDir=${HOME}/test-results -DreleaseBuild=true pkl-cli:alpineExecutableAmd64 pkl-core:testAlpineExecutableAmd64
         name: gradle buildNative
     - persist_to_workspace:
         root: '.'
         paths:
         - pkl-cli/build/executable/
-    - run:
-        command: |-
-          mkdir ~/test-results/
-          find . -type f -regex ".*/build/test-results/.*xml" -exec cp {} ~/test-results/ \;
-        name: Gather test results
-        when: always
     - store_test_results:
         path: ~/test-results
     environment:
@@ -289,6 +259,26 @@ jobs:
     resource_class: xlarge
     docker:
     - image: oraclelinux:8-slim
+  pkl-cli-windows-amd64-release:
+    steps:
+    - checkout
+    - run:
+        command: |-
+          export PATH=~/staticdeps/bin:$PATH
+          ./gradlew --info --stacktrace -DtestReportsDir=${HOME}/test-results -DreleaseBuild=true pkl-cli:windowsExecutableAmd64 pkl-core:testWindowsExecutableAmd64
+        name: gradle buildNative
+        shell: bash.exe
+    - persist_to_workspace:
+        root: '.'
+        paths:
+        - pkl-cli/build/executable/
+    - store_test_results:
+        path: ~/test-results
+    environment:
+      LANG: en_US.UTF-8
+    resource_class: windows.large
+    machine:
+      image: windows-server-2022-gui:current
   pkl-cli-macOS-amd64-snapshot:
     steps:
     - checkout
@@ -298,18 +288,12 @@ jobs:
     - run:
         command: |-
           export PATH=~/staticdeps/bin:$PATH
-          ./gradlew --info --stacktrace pkl-cli:macExecutableAmd64 pkl-core:testMacExecutableAmd64
+          ./gradlew --info --stacktrace -DtestReportsDir=${HOME}/test-results pkl-cli:macExecutableAmd64 pkl-core:testMacExecutableAmd64
         name: gradle buildNative
     - persist_to_workspace:
         root: '.'
         paths:
         - pkl-cli/build/executable/
-    - run:
-        command: |-
-          mkdir ~/test-results/
-          find . -type f -regex ".*/build/test-results/.*xml" -exec cp {} ~/test-results/ \;
-        name: Gather test results
-        when: always
     - store_test_results:
         path: ~/test-results
     environment:
@@ -380,18 +364,12 @@ jobs:
     - run:
         command: |-
           export PATH=~/staticdeps/bin:$PATH
-          ./gradlew --info --stacktrace pkl-cli:linuxExecutableAmd64 pkl-core:testLinuxExecutableAmd64
+          ./gradlew --info --stacktrace -DtestReportsDir=${HOME}/test-results pkl-cli:linuxExecutableAmd64 pkl-core:testLinuxExecutableAmd64
         name: gradle buildNative
     - persist_to_workspace:
         root: '.'
         paths:
         - pkl-cli/build/executable/
-    - run:
-        command: |-
-          mkdir ~/test-results/
-          find . -type f -regex ".*/build/test-results/.*xml" -exec cp {} ~/test-results/ \;
-        name: Gather test results
-        when: always
     - store_test_results:
         path: ~/test-results
     environment:
@@ -406,18 +384,12 @@ jobs:
     - run:
         command: |-
           export PATH=~/staticdeps/bin:$PATH
-          ./gradlew --info --stacktrace pkl-cli:macExecutableAarch64 pkl-core:testMacExecutableAarch64
+          ./gradlew --info --stacktrace -DtestReportsDir=${HOME}/test-results pkl-cli:macExecutableAarch64 pkl-core:testMacExecutableAarch64
         name: gradle buildNative
     - persist_to_workspace:
         root: '.'
         paths:
         - pkl-cli/build/executable/
-    - run:
-        command: |-
-          mkdir ~/test-results/
-          find . -type f -regex ".*/build/test-results/.*xml" -exec cp {} ~/test-results/ \;
-        name: Gather test results
-        when: always
     - store_test_results:
         path: ~/test-results
     environment:
@@ -472,18 +444,12 @@ jobs:
     - run:
         command: |-
           export PATH=~/staticdeps/bin:$PATH
-          ./gradlew --info --stacktrace pkl-cli:linuxExecutableAarch64 pkl-core:testLinuxExecutableAarch64
+          ./gradlew --info --stacktrace -DtestReportsDir=${HOME}/test-results pkl-cli:linuxExecutableAarch64 pkl-core:testLinuxExecutableAarch64
         name: gradle buildNative
     - persist_to_workspace:
         root: '.'
         paths:
         - pkl-cli/build/executable/
-    - run:
-        command: |-
-          mkdir ~/test-results/
-          find . -type f -regex ".*/build/test-results/.*xml" -exec cp {} ~/test-results/ \;
-        name: Gather test results
-        when: always
     - store_test_results:
         path: ~/test-results
     environment:
@@ -555,18 +521,12 @@ jobs:
     - run:
         command: |-
           export PATH=~/staticdeps/bin:$PATH
-          ./gradlew --info --stacktrace pkl-cli:alpineExecutableAmd64 pkl-core:testAlpineExecutableAmd64
+          ./gradlew --info --stacktrace -DtestReportsDir=${HOME}/test-results pkl-cli:alpineExecutableAmd64 pkl-core:testAlpineExecutableAmd64
         name: gradle buildNative
     - persist_to_workspace:
         root: '.'
         paths:
         - pkl-cli/build/executable/
-    - run:
-        command: |-
-          mkdir ~/test-results/
-          find . -type f -regex ".*/build/test-results/.*xml" -exec cp {} ~/test-results/ \;
-        name: Gather test results
-        when: always
     - store_test_results:
         path: ~/test-results
     environment:
@@ -575,18 +535,32 @@ jobs:
     resource_class: xlarge
     docker:
     - image: oraclelinux:8-slim
+  pkl-cli-windows-amd64-snapshot:
+    steps:
+    - checkout
+    - run:
+        command: |-
+          export PATH=~/staticdeps/bin:$PATH
+          ./gradlew --info --stacktrace -DtestReportsDir=${HOME}/test-results pkl-cli:windowsExecutableAmd64 pkl-core:testWindowsExecutableAmd64
+        name: gradle buildNative
+        shell: bash.exe
+    - persist_to_workspace:
+        root: '.'
+        paths:
+        - pkl-cli/build/executable/
+    - store_test_results:
+        path: ~/test-results
+    environment:
+      LANG: en_US.UTF-8
+    resource_class: windows.large
+    machine:
+      image: windows-server-2022-gui:current
   gradle-check-jdk17:
     steps:
     - checkout
     - run:
-        command: ./gradlew --info --stacktrace check
+        command: ./gradlew --info --stacktrace -DtestReportsDir=${HOME}/test-results check
         name: gradle check
-    - run:
-        command: |-
-          mkdir ~/test-results/
-          find . -type f -regex ".*/build/test-results/.*xml" -exec cp {} ~/test-results/ \;
-        name: Gather test results
-        when: always
     - store_test_results:
         path: ~/test-results
     environment:
@@ -597,32 +571,33 @@ jobs:
     steps:
     - checkout
     - run:
-        command: ./gradlew --info --stacktrace check
+        command: ./gradlew --info --stacktrace -DtestReportsDir=${HOME}/test-results check
         name: gradle check
-    - run:
-        command: |-
-          mkdir ~/test-results/
-          find . -type f -regex ".*/build/test-results/.*xml" -exec cp {} ~/test-results/ \;
-        name: Gather test results
-        when: always
     - store_test_results:
         path: ~/test-results
     environment:
       LANG: en_US.UTF-8
     docker:
     - image: cimg/openjdk:21.0
+  gradle-check-jdk17-windows:
+    steps:
+    - checkout
+    - run:
+        command: ./gradlew --info --stacktrace -DtestReportsDir=${HOME}/test-results check
+        name: gradle check
+    - store_test_results:
+        path: ~/test-results
+    environment:
+      LANG: en_US.UTF-8
+    resource_class: windows.large
+    machine:
+      image: windows-server-2022-gui:current
   bench:
     steps:
     - checkout
     - run:
-        command: ./gradlew --info --stacktrace bench:jmh
+        command: ./gradlew --info --stacktrace -DtestReportsDir=${HOME}/test-results bench:jmh
         name: bench:jmh
-    - run:
-        command: |-
-          mkdir ~/test-results/
-          find . -type f -regex ".*/build/test-results/.*xml" -exec cp {} ~/test-results/ \;
-        name: Gather test results
-        when: always
     - store_test_results:
         path: ~/test-results
     environment:
@@ -634,16 +609,10 @@ jobs:
     - checkout
     - run:
         command: |-
-          ./gradlew --info --stacktrace :pkl-gradle:build \
+          ./gradlew --info --stacktrace -DtestReportsDir=${HOME}/test-results :pkl-gradle:build \
             :pkl-gradle:compatibilityTestReleases \
             :pkl-gradle:compatibilityTestCandidate
         name: gradle compatibility
-    - run:
-        command: |-
-          mkdir ~/test-results/
-          find . -type f -regex ".*/build/test-results/.*xml" -exec cp {} ~/test-results/ \;
-        name: Gather test results
-        when: always
     - store_test_results:
         path: ~/test-results
     environment:
@@ -656,17 +625,11 @@ jobs:
     - attach_workspace:
         at: '.'
     - run:
-        command: ./gradlew --info --stacktrace publishToSonatype
+        command: ./gradlew --info --stacktrace -DtestReportsDir=${HOME}/test-results publishToSonatype
     - persist_to_workspace:
         root: '.'
         paths:
         - pkl-cli/build/executable/
-    - run:
-        command: |-
-          mkdir ~/test-results/
-          find . -type f -regex ".*/build/test-results/.*xml" -exec cp {} ~/test-results/ \;
-        name: Gather test results
-        when: always
     - store_test_results:
         path: ~/test-results
     environment:
@@ -679,17 +642,11 @@ jobs:
     - attach_workspace:
         at: '.'
     - run:
-        command: ./gradlew --info --stacktrace -DreleaseBuild=true publishToSonatype closeAndReleaseSonatypeStagingRepository
+        command: ./gradlew --info --stacktrace -DtestReportsDir=${HOME}/test-results -DreleaseBuild=true publishToSonatype closeAndReleaseSonatypeStagingRepository
     - persist_to_workspace:
         root: '.'
         paths:
         - pkl-cli/build/executable/
-    - run:
-        command: |-
-          mkdir ~/test-results/
-          find . -type f -regex ".*/build/test-results/.*xml" -exec cp {} ~/test-results/ \;
-        name: Gather test results
-        when: always
     - store_test_results:
         path: ~/test-results
     environment:
@@ -753,6 +710,9 @@ workflows:
     - gradle-check-jdk21:
         requires:
         - hold
+    - gradle-check-jdk17-windows:
+        requires:
+        - hold
     when:
       matches:
         value: << pipeline.git.branch >>
@@ -761,6 +721,7 @@ workflows:
     jobs:
     - gradle-check-jdk17
     - gradle-check-jdk21
+    - gradle-check-jdk17-windows
     - bench
     - gradle-compatibility
     - pkl-cli-macOS-amd64-snapshot
@@ -768,10 +729,12 @@ workflows:
     - pkl-cli-macOS-aarch64-snapshot
     - pkl-cli-linux-aarch64-snapshot
     - pkl-cli-linux-alpine-amd64-snapshot
+    - pkl-cli-windows-amd64-snapshot
     - deploy-snapshot:
         requires:
         - gradle-check-jdk17
         - gradle-check-jdk21
+        - gradle-check-jdk17-windows
         - bench
         - gradle-compatibility
         - pkl-cli-macOS-amd64-snapshot
@@ -779,6 +742,7 @@ workflows:
         - pkl-cli-macOS-aarch64-snapshot
         - pkl-cli-linux-aarch64-snapshot
         - pkl-cli-linux-alpine-amd64-snapshot
+        - pkl-cli-windows-amd64-snapshot
         context: pkl-maven-release
     - trigger-docsite-build:
         requires:
@@ -803,6 +767,12 @@ workflows:
             ignore: /.*/
           tags:
             only: /^v?\d+\.\d+\.\d+$/
+    - gradle-check-jdk17-windows:
+        filters:
+          branches:
+            ignore: /.*/
+          tags:
+            only: /^v?\d+\.\d+\.\d+$/
     - bench:
         filters:
           branches:
@@ -845,10 +815,17 @@ workflows:
             ignore: /.*/
           tags:
             only: /^v?\d+\.\d+\.\d+$/
+    - pkl-cli-windows-amd64-release:
+        filters:
+          branches:
+            ignore: /.*/
+          tags:
+            only: /^v?\d+\.\d+\.\d+$/
     - github-release:
         requires:
         - gradle-check-jdk17
         - gradle-check-jdk21
+        - gradle-check-jdk17-windows
         - bench
         - gradle-compatibility
         - pkl-cli-macOS-amd64-release
@@ -856,6 +833,7 @@ workflows:
         - pkl-cli-macOS-aarch64-release
         - pkl-cli-linux-aarch64-release
         - pkl-cli-linux-alpine-amd64-release
+        - pkl-cli-windows-amd64-release
         context: pkl-github-release
         filters:
           branches:
@@ -885,6 +863,7 @@ workflows:
     jobs:
     - gradle-check-jdk17
     - gradle-check-jdk21
+    - gradle-check-jdk17-windows
     - bench
     - gradle-compatibility
     - pkl-cli-macOS-amd64-release
@@ -892,6 +871,7 @@ workflows:
     - pkl-cli-macOS-aarch64-release
     - pkl-cli-linux-aarch64-release
     - pkl-cli-linux-alpine-amd64-release
+    - pkl-cli-windows-amd64-release
     when:
       matches:
         value: << pipeline.git.branch >>
diff --git a/.circleci/jobs/BuildNativeJob.pkl b/.circleci/jobs/BuildNativeJob.pkl
index 8ce143d5..139dd346 100644
--- a/.circleci/jobs/BuildNativeJob.pkl
+++ b/.circleci/jobs/BuildNativeJob.pkl
@@ -16,12 +16,9 @@
 /// Builds the native `pkl` CLI
 extends "GradleJob.pkl"
 
-import "package://pkg.pkl-lang.org/pkl-pantry/com.circleci.v2@1.1.0#/Config.pkl"
+import "package://pkg.pkl-lang.org/pkl-pantry/com.circleci.v2@1.1.2#/Config.pkl"
 import "package://pkg.pkl-lang.org/pkl-pantry/pkl.experimental.uri@1.0.0#/URI.pkl"
 
-/// The OS to run on
-os: "macOS"|"linux"
-
 /// The architecture to use
 arch: "amd64"|"aarch64"
 
@@ -119,10 +116,14 @@ steps {
   new Config.RunStep {
     name = "gradle buildNative"
     local _os =
-      if (os == "macOS") "mac"
+      if (module.os == "macOS") "mac"
       else if (musl) "alpine"
+      else if (module.os == "windows") "windows"
       else "linux"
     local jobName = "\(_os)Executable\(arch.capitalize())"
+    when (module.os == "windows") {
+      shell = "bash.exe"
+    }
     command = #"""
       export PATH=~/staticdeps/bin:$PATH
       ./gradlew \#(module.gradleArgs) pkl-cli:\#(jobName) pkl-core:test\#(jobName.capitalize())
@@ -142,7 +143,8 @@ job {
       xcode = "15.3.0"
     }
     resource_class = "macos.m1.large.gen1"
-  } else {
+  }
+  when (os == "linux") {
     docker {
       new {
         image = if (arch == "aarch64") "arm64v8/oraclelinux:8-slim" else "oraclelinux:8-slim"
@@ -153,4 +155,10 @@ job {
     }
     resource_class = if (arch == "aarch64") "arm.xlarge" else "xlarge"
   }
+  when (os == "windows") {
+    machine {
+      image = "windows-server-2022-gui:current"
+    }
+    resource_class = "windows.large"
+  }
 }
diff --git a/.circleci/jobs/DeployJob.pkl b/.circleci/jobs/DeployJob.pkl
index 6ad2761d..a46faea7 100644
--- a/.circleci/jobs/DeployJob.pkl
+++ b/.circleci/jobs/DeployJob.pkl
@@ -15,7 +15,7 @@
 //===----------------------------------------------------------------------===//
 extends "GradleJob.pkl"
 
-import "package://pkg.pkl-lang.org/pkl-pantry/com.circleci.v2@1.1.0#/Config.pkl"
+import "package://pkg.pkl-lang.org/pkl-pantry/com.circleci.v2@1.1.2#/Config.pkl"
 
 local self = this
 
@@ -27,6 +27,8 @@ job {
   }
 }
 
+os = "linux"
+
 steps {
   new Config.AttachWorkspaceStep { at = "." }
   new Config.RunStep {
diff --git a/.circleci/jobs/GradleCheckJob.pkl b/.circleci/jobs/GradleCheckJob.pkl
index 1e4937ea..39ab7beb 100644
--- a/.circleci/jobs/GradleCheckJob.pkl
+++ b/.circleci/jobs/GradleCheckJob.pkl
@@ -15,9 +15,11 @@
 //===----------------------------------------------------------------------===//
 extends "GradleJob.pkl"
 
-import "package://pkg.pkl-lang.org/pkl-pantry/com.circleci.v2@1.1.0#/Config.pkl"
+import "package://pkg.pkl-lang.org/pkl-pantry/com.circleci.v2@1.1.2#/Config.pkl"
 
-javaVersion: "11.0"|"17.0"|"21.0"
+javaVersion: "17.0"|"21.0"
+
+os = "linux"
 
 steps {
   new Config.RunStep {
@@ -27,9 +29,17 @@ steps {
 }
 
 job {
-  docker {
-    new {
-      image = "cimg/openjdk:\(javaVersion)"
+  when (os == "linux") {
+    docker {
+      new {
+        image = "cimg/openjdk:\(javaVersion)"
+      }
     }
   }
+  when (os == "windows") {
+    machine {
+      image = "windows-server-2022-gui:current"
+    }
+    resource_class = "windows.large"
+  }
 }
diff --git a/.circleci/jobs/GradleJob.pkl b/.circleci/jobs/GradleJob.pkl
index 298093c9..bb9c7fb1 100644
--- a/.circleci/jobs/GradleJob.pkl
+++ b/.circleci/jobs/GradleJob.pkl
@@ -15,14 +15,18 @@
 //===----------------------------------------------------------------------===//
 abstract module GradleJob
 
-import "package://pkg.pkl-lang.org/pkl-pantry/com.circleci.v2@1.1.0#/Config.pkl"
+import "package://pkg.pkl-lang.org/pkl-pantry/com.circleci.v2@1.1.2#/Config.pkl"
 
 /// Whether this is a release build or not.
 isRelease: Boolean = false
 
+/// The OS to run on
+os: "macOS"|"linux"|"windows"
+
 fixed gradleArgs = new Listing {
   "--info"
   "--stacktrace"
+  "-DtestReportsDir=${HOME}/test-results"
   when (isRelease) {
     "-DreleaseBuild=true"
   }
@@ -37,15 +41,6 @@ job: Config.Job = new {
   steps {
     "checkout"
     ...module.steps
-    new Config.RunStep {
-      // find all test results and write them to the home dir
-      name = "Gather test results"
-      command = """
-        mkdir ~/test-results/
-        find . -type f -regex ".*/build/test-results/.*xml" -exec cp {} ~/test-results/ \\;
-        """
-      `when` = "always"
-    }
     new Config.StoreTestResults {
       path = "~/test-results"
     }
diff --git a/.circleci/jobs/SimpleGradleJob.pkl b/.circleci/jobs/SimpleGradleJob.pkl
index c34f4dce..ef2526b9 100644
--- a/.circleci/jobs/SimpleGradleJob.pkl
+++ b/.circleci/jobs/SimpleGradleJob.pkl
@@ -15,12 +15,14 @@
 //===----------------------------------------------------------------------===//
 extends "GradleJob.pkl"
 
-import "package://pkg.pkl-lang.org/pkl-pantry/com.circleci.v2@1.1.0#/Config.pkl"
+import "package://pkg.pkl-lang.org/pkl-pantry/com.circleci.v2@1.1.2#/Config.pkl"
 
 name: String = command
 
 command: String
 
+os = "linux"
+
 steps {
   new Config.RunStep {
     name = module.name
diff --git a/.gitattributes b/.gitattributes
index 896495e3..39935713 100644
--- a/.gitattributes
+++ b/.gitattributes
@@ -4,3 +4,4 @@
 /docs/** linguist-documentation
 
 *.pkl linguist-language=Groovy
+* text eol=lf
diff --git a/DEVELOPMENT.adoc b/DEVELOPMENT.adoc
index a129fa4a..0f42d127 100644
--- a/DEVELOPMENT.adoc
+++ b/DEVELOPMENT.adoc
@@ -40,6 +40,7 @@ pkl-cli/build/executable/jpkl                   # run Java executable
 pkl-cli/build/executable/pkl-macos-amd64        # run Mac executable
 pkl-cli/build/executable/pkl-linux-amd64        # run Linux executable
 pkl-cli/build/executable/pkl-alpine-linux-amd64 # run Alpine Linux executable 
+pkl-cli/build/executable/pkl-windows-amd64.exe  # run Windows executable 
 ----
 
 == Update Gradle
@@ -68,6 +69,13 @@ based on version information from https://search.maven.org, https://plugins.grad
 * ANTLR code generation is performed by task `:pkl-core:generateGrammarSource`
 ** Output dir is `generated/antlr/`
 
+== Remote JVM Debugging
+
+To enable remote JVM debugging when running Gradle tasks (e.g. test), add the flag `-Djvmdebug=true`.
+This will listen on port 5005.
+
+Example: `./gradlew test -Djvmdebug=true`
+
 == Resources
 For automated build setup examples see our https://github.com/apple/pkl/blob/main/.circleci/[CircleCI] jobs like our https://github.com/apple/pkl/blob/main/.circleci/jobs/BuildNativeJob.pkl[BuildNativeJob.pkl], where we build Pkl automatically.
 
diff --git a/buildSrc/src/main/kotlin/BuildInfo.kt b/buildSrc/src/main/kotlin/BuildInfo.kt
index d293d340..0264375d 100644
--- a/buildSrc/src/main/kotlin/BuildInfo.kt
+++ b/buildSrc/src/main/kotlin/BuildInfo.kt
@@ -26,6 +26,7 @@ open class BuildInfo(project: Project) {
       when {
         os.isMacOsX -> "macos"
         os.isLinux -> "linux"
+        os.isWindows -> "windows"
         else -> throw RuntimeException("${os.familyName} is not supported.")
       }
     }
@@ -36,7 +37,8 @@ open class BuildInfo(project: Project) {
 
     val downloadUrl: String by lazy {
       val jdkMajor = graalVmJdkVersion.takeWhile { it != '.' }
-      "https://download.oracle.com/graalvm/$jdkMajor/archive/$baseName.tar.gz"
+      val extension = if (os.isWindows) "zip" else "tar.gz"
+      "https://download.oracle.com/graalvm/$jdkMajor/archive/$baseName.$extension"
     }
 
     val installDir: File by lazy {
@@ -85,9 +87,14 @@ open class BuildInfo(project: Project) {
   val commitId: String by lazy {
     // only run command once per build invocation
     if (project === project.rootProject) {
-      Runtime.getRuntime()
-        .exec(arrayOf("git", "rev-parse", "--short", "HEAD"), arrayOf(), project.rootDir)
-        .inputStream.reader().readText().trim()
+      val process = ProcessBuilder()
+        .command("git", "rev-parse", "--short", "HEAD")
+        .directory(project.rootDir)
+        .start()
+      process.waitFor().also { exitCode ->
+        if (exitCode == -1) throw RuntimeException(process.errorStream.reader().readText())
+      }
+      process.inputStream.reader().readText().trim()
     } else {
       project.rootProject.extensions.getByType(BuildInfo::class.java).commitId
     }
diff --git a/buildSrc/src/main/kotlin/ExecutableJar.kt b/buildSrc/src/main/kotlin/ExecutableJar.kt
index 70b79706..ed63a284 100644
--- a/buildSrc/src/main/kotlin/ExecutableJar.kt
+++ b/buildSrc/src/main/kotlin/ExecutableJar.kt
@@ -1,11 +1,11 @@
 import org.gradle.api.DefaultTask
 import org.gradle.api.file.RegularFileProperty
 import org.gradle.api.provider.ListProperty
+import org.gradle.api.provider.Property
 import org.gradle.api.tasks.Input
 import org.gradle.api.tasks.InputFile
 import org.gradle.api.tasks.OutputFile
 import org.gradle.api.tasks.TaskAction
-import org.gradle.kotlin.dsl.listProperty
 
 /**
  * Builds a self-contained Pkl CLI Jar that is directly executable on *nix
@@ -15,27 +15,25 @@ import org.gradle.kotlin.dsl.listProperty
  *
  * https://skife.org/java/unix/2011/06/20/really_executable_jars.html
  */
-open class ExecutableJar : DefaultTask() {
+abstract class ExecutableJar : DefaultTask() {
   @get:InputFile
-  val inJar: RegularFileProperty = project.objects.fileProperty()
+  abstract val inJar: RegularFileProperty
 
   @get:OutputFile
-  val outJar: RegularFileProperty = project.objects.fileProperty()
+  abstract val outJar: RegularFileProperty
 
   @get:Input
-  val jvmArgs: ListProperty<String> = project.objects.listProperty()
+  abstract val jvmArgs: ListProperty<String>
 
   @TaskAction
   fun buildJar() {
     val inFile = inJar.get().asFile
     val outFile = outJar.get().asFile
     val escapedJvmArgs = jvmArgs.get().joinToString(separator = " ") { "\"$it\"" }
-
     val startScript = """
       #!/bin/sh
       exec java $escapedJvmArgs -jar $0 "$@"
-    """.trim().trimMargin() + "\n\n\n"
-
+    """.trimIndent() + "\n\n\n"
     outFile.outputStream().use { outStream ->
       startScript.byteInputStream().use { it.copyTo(outStream) }
       inFile.inputStream().use { it.copyTo(outStream) }
diff --git a/buildSrc/src/main/kotlin/pklAllProjects.gradle.kts b/buildSrc/src/main/kotlin/pklAllProjects.gradle.kts
index 6ef0256e..b65b51ab 100644
--- a/buildSrc/src/main/kotlin/pklAllProjects.gradle.kts
+++ b/buildSrc/src/main/kotlin/pklAllProjects.gradle.kts
@@ -93,3 +93,28 @@ val updateDependencyLocks by tasks.registering {
 }
 
 val allDependencies by tasks.registering(DependencyReportTask::class)
+
+tasks.withType(Test::class).configureEach {
+  System.getProperty("testReportsDir")?.let { reportsDir ->
+    reports.junitXml.outputLocation.set(file(reportsDir).resolve(project.name).resolve(name))
+  }
+  debugOptions {
+    enabled = System.getProperty("jvmdebug")?.toBoolean() ?: false
+    @Suppress("UnstableApiUsage")
+    host = "*"
+    port = 5005
+    suspend = true
+    server = true
+  }
+}
+
+tasks.withType(JavaExec::class).configureEach {
+  debugOptions {
+    enabled = System.getProperty("jvmdebug")?.toBoolean() ?: false
+    @Suppress("UnstableApiUsage")
+    host = "*"
+    port = 5005
+    suspend = true
+    server = true
+  }
+}
diff --git a/buildSrc/src/main/kotlin/pklGraalVm.gradle.kts b/buildSrc/src/main/kotlin/pklGraalVm.gradle.kts
index 175c83f2..eaf5a632 100644
--- a/buildSrc/src/main/kotlin/pklGraalVm.gradle.kts
+++ b/buildSrc/src/main/kotlin/pklGraalVm.gradle.kts
@@ -2,6 +2,7 @@ import java.nio.file.*
 import java.util.UUID
 import de.undercouch.gradle.tasks.download.Download
 import de.undercouch.gradle.tasks.download.Verify
+import kotlin.io.path.createDirectories
 
 plugins {
   id("de.undercouch.download")
@@ -9,7 +10,10 @@ plugins {
 
 val buildInfo = project.extensions.getByType<BuildInfo>()
 
-val BuildInfo.GraalVm.downloadFile get() = file(homeDir).resolve("${baseName}.tar.gz")
+val BuildInfo.GraalVm.downloadFile get(): File {
+  val extension = if (buildInfo.os.isWindows) "zip" else "tar.gz"
+  return file(homeDir).resolve("${baseName}.$extension")
+}
 
 // tries to minimize chance of corruption by download-to-temp-file-and-move
 val downloadGraalVmAarch64 by tasks.registering(Download::class) {
@@ -72,11 +76,10 @@ fun Task.configureInstallGraalVm(graalVm: BuildInfo.GraalVm) {
   }
 
   doLast {
-    val distroDir = "${graalVm.homeDir}/${UUID.randomUUID()}"
+    val distroDir = Paths.get(graalVm.homeDir, UUID.randomUUID().toString())
 
     try {
-      mkdir(distroDir)
-
+      distroDir.createDirectories()
       println("Extracting ${graalVm.downloadFile} into $distroDir")
       // faster and more reliable than Gradle's `copy { from tarTree() }`
       exec {
@@ -85,17 +88,18 @@ fun Task.configureInstallGraalVm(graalVm: BuildInfo.GraalVm) {
         args("--strip-components=1", "-xzf", graalVm.downloadFile)
       }
 
-      val distroBinDir = if (buildInfo.os.isMacOsX) "$distroDir/Contents/Home/bin" else "$distroDir/bin"
+      val distroBinDir = if (buildInfo.os.isMacOsX) distroDir.resolve("Contents/Home/bin") else distroDir.resolve("bin")
 
       println("Installing native-image into $distroDir")
       exec {
-        executable = "$distroBinDir/gu"
+        val executableName = if (buildInfo.os.isWindows) "gu.cmd" else "gu"
+        executable = distroBinDir.resolve(executableName).toString()
         args("install", "--no-progress", "native-image")
       }
 
       println("Creating symlink ${graalVm.installDir} for $distroDir")
-      val tempLink = Paths.get("${graalVm.homeDir}/${UUID.randomUUID()}")
-      Files.createSymbolicLink(tempLink, Paths.get(distroDir))
+      val tempLink = Paths.get(graalVm.homeDir, UUID.randomUUID().toString())
+      Files.createSymbolicLink(tempLink, distroDir)
       try {
         Files.move(tempLink, graalVm.installDir.toPath(), StandardCopyOption.ATOMIC_MOVE)
       } catch (e: Exception) {
diff --git a/docs/modules/language-reference/pages/index.adoc b/docs/modules/language-reference/pages/index.adoc
index 8e1e38c7..b409b4bf 100644
--- a/docs/modules/language-reference/pages/index.adoc
+++ b/docs/modules/language-reference/pages/index.adoc
@@ -2140,9 +2140,18 @@ For example, a module with URI `modulepath:/animals/birds/pigeon.pkl`
 can import `modulepath:/animals/birds/parrot.pkl`
 with `import "parrot.pkl"` or `import "/animals/birds/parrot.pkl"`.
 
-NOTE: When importing a relative folder or file that starts with `@`, the import string must be prefixed with `./`.
-Otherwise, this syntax will be interpreted as dependency notation.
+[NOTE]
+.Paths on Windows
+====
+Relative paths use the `/` character as the directory separator on all platforms, including Windows.
 
+Paths that contain drive letters (e.g. `C:`) must be declared as an absolute file URI, for example: `import "file:///C:/path/to/my/module.pkl"`. Otherwise, they are interpreted as a URI scheme.
+====
+
+NOTE: When importing a relative directory or file that starts with `@`, the import string must be prefixed with `./`.
+Otherwise, this syntax will be interpreted as xref:dependency-notation[dependency notation].
+
+[#dependency-notation]
 ==== Dependency notation URIs
 
 Example: `+@birds/bird.pkl+`
diff --git a/docs/modules/pkl-cli/pages/index.adoc b/docs/modules/pkl-cli/pages/index.adoc
index 02b36513..5f4e1001 100644
--- a/docs/modules/pkl-cli/pages/index.adoc
+++ b/docs/modules/pkl-cli/pages/index.adoc
@@ -8,6 +8,7 @@ include::ROOT:partial$component-attributes.adoc[]
 :uri-pkl-linux-amd64-download: {uri-sonatype-snapshot-download}&a=pkl-cli-linux-amd64&e=bin
 :uri-pkl-linux-aarch64-download: {uri-sonatype-snapshot-download}&a=pkl-cli-linux-aarch64&e=bin
 :uri-pkl-alpine-download: {uri-sonatype-snapshot-download}&a=pkl-cli-alpine-linux-amd64&e=bin
+:uri-pkl-windows-download: {uri-sonatype-snapshot-download}&a=pkl-cli-windows-amd64&e=exe
 :uri-pkl-java-download: {uri-sonatype-snapshot-download}&a=pkl-cli-java&e=jar
 
 ifdef::is-release-version[]
@@ -16,6 +17,7 @@ ifdef::is-release-version[]
 :uri-pkl-linux-amd64-download: {github-releases}/pkl-linux-amd64
 :uri-pkl-linux-aarch64-download: {github-releases}/pkl-linux-aarch64
 :uri-pkl-alpine-download: {github-releases}/pkl-alpine-linux-amd64
+:uri-pkl-windows-download: {github-releases}/pkl-windows-amd64.exe
 :uri-pkl-java-download: {uri-maven-repo}/org/pkl-lang/pkl-cli-java/{pkl-artifact-version}/pkl-cli-java-{pkl-artifact-version}.jar
 endif::[]
 
@@ -37,9 +39,10 @@ The CLI comes in multiple flavors:
 * Native Linux executable for amd64
 * Native Linux executable for aarch64
 * Native Alpine Linux executable for amd64 (cross-compiled and tested on Oracle Linux 8)
-* Java executable (tested with Java 17/21 on macOS and Oracle Linux, may work on other platforms)
+* Native Windows executable for amd64 (tested on Windows Server 2022)
+* Java executable (tested with Java 17/21 on macOS and Oracle Linux)
 
-On macOS and Linux, we recommend using the native executables.
+On macOS, Linux, and Windows, we recommend using the native executables.
 They are self-contained, start up instantly, and run complex Pkl code much faster than the Java executable.
 
 .What is the Difference Between the Linux and Alpine Linux Executables?
@@ -59,7 +62,7 @@ Except where noted otherwise, the rest of this page discusses the native executa
 [[homebrew]]
 === Homebrew
 
-Release versions can be installed with {uri-homebrew}[Homebrew].
+On macOS and Linux, release versions can be installed with {uri-homebrew}[Homebrew].
 
 ifdef::is-release-version[]
 To install Pkl, run:
@@ -111,7 +114,7 @@ chmod +x pkl
 
 This should print something similar to:
 
-[source,shell]
+[source]
 [subs="+attributes"]
 ----
 Pkl {pkl-version} (macOS, native)
@@ -145,7 +148,7 @@ chmod +x pkl
 
 This should print something similar to:
 
-[source,shell]
+[source]
 [subs="+attributes"]
 ----
 Pkl {pkl-version} (Linux, native)
@@ -167,7 +170,7 @@ chmod +x pkl
 
 This should print something similar to:
 
-[source,shell]
+[source]
 [subs="+attributes"]
 ----
 Pkl {pkl-version} (Linux, native)
@@ -175,6 +178,23 @@ Pkl {pkl-version} (Linux, native)
 
 NOTE: We currently do not support the aarch64 architecture for Alpine Linux.
 
+=== Windows Executable
+
+[source,PowerShell]
+[subs="+attributes"]
+----
+Invoke-WebRequest '{uri-pkl-windows-download}' -OutFile pkl.exe
+.\pkl --version
+----
+
+[source]
+[subs="+attributes"]
+----
+Pkl {pkl-version} (Windows 10.0, native)
+----
+
+NOTE: We currently do not support the aarch64 architecture for Windows.
+
 === Java Executable
 
 [source,shell]
@@ -193,27 +213,8 @@ This should print something similar to:
 Pkl {pkl-version} (macOS 14.2, Java 17.0.10)
 ----
 
-=== Windows support
-Pkl does not currently support running natively on Windows. Pkl has been reported to work on the https://learn.microsoft.com/en-us/windows/wsl/install[Windows Subsystem for Linux] and on a https://www.oracle.com/java/technologies/downloads/#jdk21-windows[Java Runtime] using https://search.maven.org/remote_content?g=org.pkl-lang&a=pkl-cli-java&v=LATEST[`jpkl` (the Java executable version of Pkl)].
-
-The following is from successful uses of `jpkl` on Windows:
-[source,shell]
-[subs="+attributes"]
-----
-> java -jar pkl-cli-java.jar --version
-Pkl 0.26.0-dev+21e0e14 (Windows 10 10.0, Java 21.0.2)
-----
-
-Note: You must use forward slashes in all paths for Windows with absolute paths prefixed with file:///.  The following examples are valid:
-[source,shell]
-[subs="+attributes"]
-----
-> java -jar pkl-cli-java.jar eval file:///C:/Code/pkl/test.pkl
-> java -jar pkl-cli-java.jar eval ../Code/pkl/test.pkl
-> java -jar pkl-cli-java.jar eval pkl/test.pkl
-----
-https://github.com/apple/pkl/issues/20[GitHub Issue #20] is used to track progress on support for the Windows platform.
-
+NOTE: The Java executable does not work as an executable file on Windows.
+However, it will work as a jar, for example, with `java -jar jpkl`.
 
 [[usage]]
 == Usage
diff --git a/gradle/libs.versions.toml b/gradle/libs.versions.toml
index 92e5c831..e0d2e7a6 100644
--- a/gradle/libs.versions.toml
+++ b/gradle/libs.versions.toml
@@ -15,6 +15,7 @@ graalVmSha256-macos-x64 = "14f4bd6417809905f86e786c779d0fc2feb840d7dac35ae3503eb
 graalVmSha256-macos-aarch64 = "e944c5ce5da56e683fc8f1a57191b46d9cb702930b1688bda064fcf467d876b8"
 graalVmSha256-linux-x64 = "112dc9b92d81a946f1b5b334646151b790785c813e76fcf13527a319003d7e2c"
 graalVmSha256-linux-aarch64 = "c95ac550d070f06666cf8c1023a098380dd565be00866473caf6ff1b7cdf680c"
+graalVmSha256-windows-x64 = "1ab2291e71f54d73e3e57b7fccbf184cabcba37e16ca9d1cf42d08474a7c02f0"
 ideaExtPlugin = "1.1"
 javaPoet = "1.+"
 javaxInject = "1"
diff --git a/pkl-cli/pkl-cli.gradle.kts b/pkl-cli/pkl-cli.gradle.kts
index c9006431..692abd3b 100644
--- a/pkl-cli/pkl-cli.gradle.kts
+++ b/pkl-cli/pkl-cli.gradle.kts
@@ -33,6 +33,7 @@ val stagedMacAarch64Executable: Configuration by configurations.creating
 val stagedLinuxAmd64Executable: Configuration by configurations.creating
 val stagedLinuxAarch64Executable: Configuration by configurations.creating
 val stagedAlpineLinuxAmd64Executable: Configuration by configurations.creating
+val stagedWindowsAmd64Executable: Configuration by configurations.creating
 
 dependencies {
   compileOnly(libs.svm)
@@ -63,6 +64,7 @@ dependencies {
   stagedLinuxAmd64Executable(executableDir("pkl-linux-amd64"))
   stagedLinuxAarch64Executable(executableDir("pkl-linux-aarch64"))
   stagedAlpineLinuxAmd64Executable(executableDir("pkl-alpine-linux-amd64"))
+  stagedWindowsAmd64Executable(executableDir("pkl-windows-amd64.exe"))
 }
 
 tasks.jar {
@@ -121,12 +123,17 @@ val testStartJavaExecutable by tasks.registering(Exec::class) {
   dependsOn(javaExecutable)
   val outputFile = layout.buildDirectory.file("testStartJavaExecutable") // dummy output to satisfy up-to-date check
   outputs.file(outputFile)
-  
-  executable = javaExecutable.get().outputs.files.singleFile.toString()
-  args("--version")
-  
+
+  if (buildInfo.os.isWindows) {
+    executable = "java"
+    args("-jar", javaExecutable.get().outputs.files.singleFile.toString(), "--version")
+  } else {
+    executable = javaExecutable.get().outputs.files.singleFile.toString()
+    args("--version")
+  }
+
   doFirst { outputFile.get().asFile.delete() }
-  
+
   doLast { outputFile.get().asFile.writeText("OK") }
 }
 
@@ -141,12 +148,13 @@ fun Exec.configureExecutable(
 ) {
   inputs.files(sourceSets.main.map { it.output }).withPropertyName("mainSourceSets").withPathSensitivity(PathSensitivity.RELATIVE)
   inputs.files(configurations.runtimeClasspath).withPropertyName("runtimeClasspath").withNormalizer(ClasspathNormalizer::class)
-  inputs.files(file(graalVm.baseDir).resolve("bin/native-image")).withPropertyName("graalVmNativeImage").withPathSensitivity(PathSensitivity.ABSOLUTE)
+  val nativeImageCommandName = if (buildInfo.os.isWindows) "native-image.cmd" else "native-image"
+  inputs.files(file(graalVm.baseDir).resolve("bin/$nativeImageCommandName")).withPropertyName("graalVmNativeImage").withPathSensitivity(PathSensitivity.ABSOLUTE)
   outputs.file(outputFile)
   outputs.cacheIf { true }
 
   workingDir(outputFile.map { it.asFile.parentFile })
-  executable = "${graalVm.baseDir}/bin/native-image"
+  executable = "${graalVm.baseDir}/bin/$nativeImageCommandName"
 
   // JARs to exclude from the class path for the native-image build.
   val exclusions = listOf(libs.truffleApi, libs.graalSdk).map { it.get().module.name }
@@ -276,6 +284,15 @@ val alpineExecutableAmd64: TaskProvider<Exec> by tasks.registering(Exec::class)
   )
 }
 
+val windowsExecutableAmd64: TaskProvider<Exec> by tasks.registering(Exec::class) {
+  dependsOn(":installGraalVmAmd64")
+  configureExecutable(
+    buildInfo.graalVmAmd64,
+    layout.buildDirectory.file("executable/pkl-windows-amd64"),
+    listOf("-Dfile.encoding=UTF-8")
+  )
+}
+
 tasks.assembleNative {
   when {
     buildInfo.os.isMacOsX -> {
@@ -284,6 +301,9 @@ tasks.assembleNative {
         dependsOn(macExecutableAarch64)
       }
     }
+    buildInfo.os.isWindows -> {
+      dependsOn(windowsExecutableAmd64)
+    }
     buildInfo.os.isLinux && buildInfo.arch == "aarch64" -> {
       dependsOn(linuxExecutableAarch64)
     }
@@ -393,6 +413,20 @@ publishing {
         description.set("Native Pkl CLI executable for linux/amd64 and statically linked to musl.")
       }
     }
+
+    create<MavenPublication>("windowsExecutableAmd64") {
+      artifactId = "pkl-cli-windows-amd64"
+      artifact(stagedWindowsAmd64Executable.singleFile) {
+        classifier = null
+        extension = "exe"
+        builtBy(stagedWindowsAmd64Executable)
+      }
+      pom {
+        name.set("pkl-cli-windows-amd64")
+        url.set("https://github.com/apple/pkl/tree/main/pkl-cli")
+        description.set("Native Pkl CLI executable for windows/amd64.")
+      }
+    }
   }
 }
 
@@ -403,5 +437,6 @@ signing {
   sign(publishing.publications["macExecutableAarch64"])
   sign(publishing.publications["macExecutableAmd64"])
   sign(publishing.publications["alpineLinuxExecutableAmd64"])
+  sign(publishing.publications["windowsExecutableAmd64"])
 }
 //endregion
diff --git a/pkl-cli/src/main/kotlin/org/pkl/cli/CliEvaluator.kt b/pkl-cli/src/main/kotlin/org/pkl/cli/CliEvaluator.kt
index bcb7841d..96d02a3b 100644
--- a/pkl-cli/src/main/kotlin/org/pkl/cli/CliEvaluator.kt
+++ b/pkl-cli/src/main/kotlin/org/pkl/cli/CliEvaluator.kt
@@ -111,7 +111,9 @@ constructor(
 
     return moduleUris.associateWith { uri ->
       val moduleDir: String? =
-        IoUtils.toPath(uri)?.let { workingDir.relativize(it.parent).toString().ifEmpty { "." } }
+        IoUtils.toPath(uri)?.let {
+          IoUtils.relativize(it.parent, workingDir).toString().ifEmpty { "." }
+        }
       val moduleKey =
         try {
           moduleResolver.resolve(uri)
@@ -158,7 +160,7 @@ constructor(
           } else {
             if (output.isNotEmpty()) {
               outputFile.writeString(
-                options.moduleOutputSeparator + IoUtils.getLineSeparator(),
+                options.moduleOutputSeparator + '\n',
                 Charsets.UTF_8,
                 StandardOpenOption.WRITE,
                 StandardOpenOption.APPEND
@@ -192,6 +194,14 @@ constructor(
     if (uri == VmUtils.REPL_TEXT_URI) ModuleSource.create(uri, reader.readText())
     else ModuleSource.uri(uri)
 
+  private fun checkPathSpec(pathSpec: String) {
+    val illegal = pathSpec.indexOfFirst { IoUtils.isReservedFilenameChar(it) && it != '/' }
+    if (illegal == -1) {
+      return
+    }
+    throw CliException("Path spec `$pathSpec` contains illegal character `${pathSpec[illegal]}`.")
+  }
+
   /**
    * Renders each module's `output.files`, writing each entry as a file into the specified output
    * directory.
@@ -207,6 +217,7 @@ constructor(
       val moduleSource = toModuleSource(moduleUri, consoleReader)
       val output = evaluator.evaluateOutputFiles(moduleSource)
       for ((pathSpec, fileOutput) in output) {
+        checkPathSpec(pathSpec)
         val resolvedPath = outputDir.resolve(pathSpec).normalize()
         val realPath = if (resolvedPath.exists()) resolvedPath.toRealPath() else resolvedPath
         if (!realPath.startsWith(outputDir)) {
@@ -228,7 +239,10 @@ constructor(
         writtenFiles[realPath] = OutputFile(pathSpec, moduleUri)
         realPath.createParentDirectories()
         realPath.writeString(fileOutput.text)
-        consoleWriter.write(currentWorkingDir.relativize(resolvedPath).toString() + "\n")
+        consoleWriter.write(
+          IoUtils.relativize(resolvedPath, currentWorkingDir).toString() +
+            IoUtils.getLineSeparator()
+        )
         consoleWriter.flush()
       }
     }
diff --git a/pkl-cli/src/main/kotlin/org/pkl/cli/CliPackageDownloader.kt b/pkl-cli/src/main/kotlin/org/pkl/cli/CliPackageDownloader.kt
index e8042d08..ac77234d 100644
--- a/pkl-cli/src/main/kotlin/org/pkl/cli/CliPackageDownloader.kt
+++ b/pkl-cli/src/main/kotlin/org/pkl/cli/CliPackageDownloader.kt
@@ -42,7 +42,11 @@ class CliPackageDownloader(
     }
     when (errors.size) {
       0 -> return
-      1 -> throw CliException(errors.values.single().message!!)
+      1 ->
+        throw CliException(
+          errors.values.single().message
+            ?: ("An unexpected error occurred: " + errors.values.single())
+        )
       else ->
         throw CliException(
           buildString {
diff --git a/pkl-cli/src/main/kotlin/org/pkl/cli/commands/TestCommand.kt b/pkl-cli/src/main/kotlin/org/pkl/cli/commands/TestCommand.kt
index cd0ae557..0e5f66d5 100644
--- a/pkl-cli/src/main/kotlin/org/pkl/cli/commands/TestCommand.kt
+++ b/pkl-cli/src/main/kotlin/org/pkl/cli/commands/TestCommand.kt
@@ -22,6 +22,7 @@ import com.github.ajalt.clikt.parameters.groups.provideDelegate
 import java.net.URI
 import org.pkl.cli.CliTestRunner
 import org.pkl.commons.cli.commands.BaseCommand
+import org.pkl.commons.cli.commands.BaseOptions
 import org.pkl.commons.cli.commands.ProjectOptions
 import org.pkl.commons.cli.commands.TestOptions
 
@@ -29,7 +30,7 @@ class TestCommand(helpLink: String) :
   BaseCommand(name = "test", help = "Run tests within the given module(s)", helpLink = helpLink) {
   val modules: List<URI> by
     argument(name = "<modules>", help = "Module paths or URIs to evaluate.")
-      .convert { parseModuleName(it) }
+      .convert { BaseOptions.parseModuleName(it) }
       .multiple()
 
   private val projectOptions by ProjectOptions()
diff --git a/pkl-cli/src/test/kotlin/org/pkl/cli/CliEvaluatorTest.kt b/pkl-cli/src/test/kotlin/org/pkl/cli/CliEvaluatorTest.kt
index 2ca85e72..44c9aa12 100644
--- a/pkl-cli/src/test/kotlin/org/pkl/cli/CliEvaluatorTest.kt
+++ b/pkl-cli/src/test/kotlin/org/pkl/cli/CliEvaluatorTest.kt
@@ -28,6 +28,9 @@ import org.junit.jupiter.api.AfterAll
 import org.junit.jupiter.api.AfterEach
 import org.junit.jupiter.api.Test
 import org.junit.jupiter.api.assertThrows
+import org.junit.jupiter.api.condition.DisabledOnOs
+import org.junit.jupiter.api.condition.EnabledOnOs
+import org.junit.jupiter.api.condition.OS
 import org.junit.jupiter.api.io.TempDir
 import org.junit.jupiter.params.ParameterizedTest
 import org.junit.jupiter.params.provider.EnumSource
@@ -424,7 +427,10 @@ result = someLib.x
     checkOutputFile(outputFiles[0], "result.pcf", contents)
   }
 
+  // Can't reliably create symlinks on Windows.
+  // Might get errors like "A required privilege is not held by the client".
   @Test
+  @DisabledOnOs(OS.WINDOWS)
   fun `moduleDir is relative to workingDir even through symlinks`() {
     val contents = "foo = 42"
     val realWorkingDir = tempDir.resolve("workingDir").createDirectories()
@@ -978,6 +984,56 @@ result = someLib.x
       .hasMessageContaining("resolve to the same file path")
   }
 
+  @Test
+  @EnabledOnOs(OS.WINDOWS)
+  fun `multiple-file output throws when using invalid Windows characters`() {
+    val moduleUri =
+      writePklFile(
+        "test.pkl",
+        """
+      output {
+        files {
+          ["foo:bar"] { text = "bar" }
+        }
+      }
+    """
+          .trimIndent()
+      )
+
+    val options =
+      CliEvaluatorOptions(
+        CliBaseOptions(sourceModules = listOf(moduleUri), workingDir = tempDir),
+        multipleFileOutputPath = ".output"
+      )
+    assertThatCode { evalToConsole(options) }
+      .hasMessageContaining("Path spec `foo:bar` contains illegal character `:`.")
+  }
+
+  @Test
+  @EnabledOnOs(OS.WINDOWS)
+  fun `multiple-file output - cannot use backslash as dir separator on Windows`() {
+    val moduleUri =
+      writePklFile(
+        "test.pkl",
+        """
+      output {
+        files {
+          ["foo\\bar"] { text = "bar" }
+        }
+      }
+    """
+          .trimIndent()
+      )
+
+    val options =
+      CliEvaluatorOptions(
+        CliBaseOptions(sourceModules = listOf(moduleUri), workingDir = tempDir),
+        multipleFileOutputPath = ".output"
+      )
+    assertThatCode { evalToConsole(options) }
+      .hasMessageContaining("Path spec `foo\\bar` contains illegal character `\\`.")
+  }
+
   @Test
   fun `evaluate output expression`() {
     val moduleUri =
diff --git a/pkl-cli/src/test/kotlin/org/pkl/cli/CliMainTest.kt b/pkl-cli/src/test/kotlin/org/pkl/cli/CliMainTest.kt
index f07dca5c..bb567724 100644
--- a/pkl-cli/src/test/kotlin/org/pkl/cli/CliMainTest.kt
+++ b/pkl-cli/src/test/kotlin/org/pkl/cli/CliMainTest.kt
@@ -24,6 +24,8 @@ import org.assertj.core.api.Assertions.assertThat
 import org.assertj.core.api.AssertionsForClassTypes.assertThatCode
 import org.junit.jupiter.api.Test
 import org.junit.jupiter.api.assertThrows
+import org.junit.jupiter.api.condition.DisabledOnOs
+import org.junit.jupiter.api.condition.OS
 import org.junit.jupiter.api.io.TempDir
 import org.pkl.cli.commands.EvalCommand
 import org.pkl.cli.commands.RootCommand
@@ -54,7 +56,10 @@ class CliMainTest {
     assertThatCode { cmd.parse(arrayOf("eval")) }.hasMessage("""Missing argument "<modules>"""")
   }
 
+  // Can't reliably create symlinks on Windows.
+  // Might get errors like "A required privilege is not held by the client".
   @Test
+  @DisabledOnOs(OS.WINDOWS)
   fun `output to symlinked directory works`(@TempDir tempDir: Path) {
     val code =
       """
diff --git a/pkl-cli/src/test/kotlin/org/pkl/cli/CliProjectPackagerTest.kt b/pkl-cli/src/test/kotlin/org/pkl/cli/CliProjectPackagerTest.kt
index 5d25c225..38fea778 100644
--- a/pkl-cli/src/test/kotlin/org/pkl/cli/CliProjectPackagerTest.kt
+++ b/pkl-cli/src/test/kotlin/org/pkl/cli/CliProjectPackagerTest.kt
@@ -15,6 +15,7 @@
  */
 package org.pkl.cli
 
+import java.io.File
 import java.io.StringWriter
 import java.net.URI
 import java.nio.file.FileSystems
@@ -27,6 +28,8 @@ import org.assertj.core.api.Assertions.assertThatCode
 import org.junit.jupiter.api.AfterAll
 import org.junit.jupiter.api.Test
 import org.junit.jupiter.api.assertThrows
+import org.junit.jupiter.api.condition.DisabledOnOs
+import org.junit.jupiter.api.condition.OS
 import org.junit.jupiter.api.io.TempDir
 import org.pkl.commons.cli.CliBaseOptions
 import org.pkl.commons.cli.CliException
@@ -35,6 +38,7 @@ import org.pkl.commons.readString
 import org.pkl.commons.test.FileTestUtils
 import org.pkl.commons.test.PackageServer
 import org.pkl.commons.writeString
+import org.pkl.core.util.IoUtils
 
 class CliProjectPackagerTest {
   companion object {
@@ -690,7 +694,11 @@ class CliProjectPackagerTest {
       )
   }
 
+  // Absolute path imports on Windows must use an absolute URI (e.g. file:///C:/Foo/Bar), because
+  // they must contain drive letters, which conflict with schemes.
+  // We skip validation for absolute URIs, so effectively we skip this check on Windows.
   @Test
+  @DisabledOnOs(OS.WINDOWS)
   fun `import path verification -- absolute import from root dir`(@TempDir tempDir: Path) {
     tempDir.writeFile(
       "main.pkl",
@@ -738,6 +746,7 @@ class CliProjectPackagerTest {
   }
 
   @Test
+  @DisabledOnOs(OS.WINDOWS)
   fun `import path verification -- absolute read from root dir`(@TempDir tempDir: Path) {
     tempDir.writeFile(
       "main.pkl",
@@ -858,17 +867,18 @@ class CliProjectPackagerTest {
         consoleWriter = out
       )
       .run()
+    val sep = File.separatorChar
     assertThat(out.toString())
-      .isEqualTo(
+      .isEqualToNormalizingNewlines(
         """
-      .out/project1@1.0.0/project1@1.0.0.zip
-      .out/project1@1.0.0/project1@1.0.0.zip.sha256
-      .out/project1@1.0.0/project1@1.0.0
-      .out/project1@1.0.0/project1@1.0.0.sha256
-      .out/project2@2.0.0/project2@2.0.0.zip
-      .out/project2@2.0.0/project2@2.0.0.zip.sha256
-      .out/project2@2.0.0/project2@2.0.0
-      .out/project2@2.0.0/project2@2.0.0.sha256
+      .out${sep}project1@1.0.0${sep}project1@1.0.0.zip
+      .out${sep}project1@1.0.0${sep}project1@1.0.0.zip.sha256
+      .out${sep}project1@1.0.0${sep}project1@1.0.0
+      .out${sep}project1@1.0.0${sep}project1@1.0.0.sha256
+      .out${sep}project2@2.0.0${sep}project2@2.0.0.zip
+      .out${sep}project2@2.0.0${sep}project2@2.0.0.zip.sha256
+      .out${sep}project2@2.0.0${sep}project2@2.0.0
+      .out${sep}project2@2.0.0${sep}project2@2.0.0.sha256
 
     """
           .trimIndent()
@@ -956,13 +966,14 @@ class CliProjectPackagerTest {
         consoleWriter = out
       )
       .run()
+    val sep = File.separatorChar
     assertThat(out.toString())
-      .isEqualTo(
+      .isEqualToNormalizingNewlines(
         """
-      .out/mangos@1.0.0/mangos@1.0.0.zip
-      .out/mangos@1.0.0/mangos@1.0.0.zip.sha256
-      .out/mangos@1.0.0/mangos@1.0.0
-      .out/mangos@1.0.0/mangos@1.0.0.sha256
+      .out${sep}mangos@1.0.0${sep}mangos@1.0.0.zip
+      .out${sep}mangos@1.0.0${sep}mangos@1.0.0.zip.sha256
+      .out${sep}mangos@1.0.0${sep}mangos@1.0.0
+      .out${sep}mangos@1.0.0${sep}mangos@1.0.0.sha256
 
     """
           .trimIndent()
@@ -971,7 +982,7 @@ class CliProjectPackagerTest {
 
   private fun Path.zipFilePaths(): List<String> {
     return FileSystems.newFileSystem(URI("jar:${toUri()}"), emptyMap<String, String>()).use { fs ->
-      Files.walk(fs.getPath("/")).map { it.toString() }.collect(Collectors.toList())
+      Files.walk(fs.getPath("/")).map(IoUtils::toNormalizedPathString).collect(Collectors.toList())
     }
   }
 }
diff --git a/pkl-cli/src/test/kotlin/org/pkl/cli/CliProjectResolverTest.kt b/pkl-cli/src/test/kotlin/org/pkl/cli/CliProjectResolverTest.kt
index e5e45b3d..4b4f654a 100644
--- a/pkl-cli/src/test/kotlin/org/pkl/cli/CliProjectResolverTest.kt
+++ b/pkl-cli/src/test/kotlin/org/pkl/cli/CliProjectResolverTest.kt
@@ -15,6 +15,7 @@
  */
 package org.pkl.cli
 
+import java.io.File
 import java.io.StringWriter
 import java.nio.file.Path
 import org.assertj.core.api.Assertions.assertThat
@@ -26,6 +27,7 @@ import org.pkl.commons.cli.CliBaseOptions
 import org.pkl.commons.cli.CliException
 import org.pkl.commons.test.FileTestUtils
 import org.pkl.commons.test.PackageServer
+import org.pkl.core.util.IoUtils
 
 class CliProjectResolverTest {
   companion object {
@@ -354,7 +356,7 @@ class CliProjectResolverTest {
       )
     assertThat(errOut.toString())
       .isEqualTo(
-        "WARN: local dependency `package://localhost:0/fruit@1.0.0` was overridden to remote dependency `package://localhost:0/fruit@1.0.5`.\n"
+        "WARN: local dependency `package://localhost:0/fruit@1.0.0` was overridden to remote dependency `package://localhost:0/fruit@1.0.5`.${IoUtils.getLineSeparator()}"
       )
   }
 
@@ -401,11 +403,12 @@ class CliProjectResolverTest {
         errWriter = errOut
       )
       .run()
+    val sep = File.separatorChar
     assertThat(consoleOut.toString())
-      .isEqualTo(
+      .isEqualToNormalizingNewlines(
         """
-      $tempDir/project1/PklProject.deps.json
-      $tempDir/project2/PklProject.deps.json
+      $tempDir${sep}project1${sep}PklProject.deps.json
+      $tempDir${sep}project2${sep}PklProject.deps.json
     
     """
           .trimIndent()
diff --git a/pkl-commons-cli/src/main/kotlin/org/pkl/commons/cli/commands/BaseCommand.kt b/pkl-commons-cli/src/main/kotlin/org/pkl/commons/cli/commands/BaseCommand.kt
index f5ae90b3..71527552 100644
--- a/pkl-commons-cli/src/main/kotlin/org/pkl/commons/cli/commands/BaseCommand.kt
+++ b/pkl-commons-cli/src/main/kotlin/org/pkl/commons/cli/commands/BaseCommand.kt
@@ -17,11 +17,6 @@ package org.pkl.commons.cli.commands
 
 import com.github.ajalt.clikt.core.CliktCommand
 import com.github.ajalt.clikt.parameters.groups.provideDelegate
-import java.net.URI
-import java.net.URISyntaxException
-import org.pkl.commons.cli.CliException
-import org.pkl.core.runtime.VmUtils
-import org.pkl.core.util.IoUtils
 
 abstract class BaseCommand(name: String, helpLink: String, help: String = "") :
   CliktCommand(
@@ -30,30 +25,4 @@ abstract class BaseCommand(name: String, helpLink: String, help: String = "") :
     epilog = "For more information, visit $helpLink",
   ) {
   val baseOptions by BaseOptions()
-
-  /**
-   * Parses [moduleName] into a URI. If scheme is not present, we expect that this is a file path
-   * and encode any possibly invalid characters. If a scheme is present, we expect that this is a
-   * valid URI.
-   */
-  protected fun parseModuleName(moduleName: String): URI =
-    when (moduleName) {
-      "-" -> VmUtils.REPL_TEXT_URI
-      else ->
-        try {
-          IoUtils.toUri(moduleName)
-        } catch (e: URISyntaxException) {
-          val message = buildString {
-            append("Module URI `$moduleName` has invalid syntax (${e.reason}).")
-            if (e.index > -1) {
-              append("\n\n")
-              append(moduleName)
-              append("\n")
-              append(" ".repeat(e.index))
-              append("^")
-            }
-          }
-          throw CliException(message)
-        }
-    }
 }
diff --git a/pkl-commons-cli/src/main/kotlin/org/pkl/commons/cli/commands/BaseOptions.kt b/pkl-commons-cli/src/main/kotlin/org/pkl/commons/cli/commands/BaseOptions.kt
index de65e545..038d76d7 100644
--- a/pkl-commons-cli/src/main/kotlin/org/pkl/commons/cli/commands/BaseOptions.kt
+++ b/pkl-commons-cli/src/main/kotlin/org/pkl/commons/cli/commands/BaseOptions.kt
@@ -22,14 +22,50 @@ import com.github.ajalt.clikt.parameters.types.long
 import com.github.ajalt.clikt.parameters.types.path
 import java.io.File
 import java.net.URI
+import java.net.URISyntaxException
 import java.nio.file.Path
 import java.time.Duration
 import java.util.regex.Pattern
 import org.pkl.commons.cli.CliBaseOptions
+import org.pkl.commons.cli.CliException
+import org.pkl.core.runtime.VmUtils
 import org.pkl.core.util.IoUtils
 
 @Suppress("MemberVisibilityCanBePrivate")
 class BaseOptions : OptionGroup() {
+  companion object {
+    /**
+     * Parses [moduleName] into a URI. If scheme is not present, we expect that this is a file path
+     * and encode any possibly invalid characters, and also normalize directory separators. If a
+     * scheme is present, we expect that this is a valid URI.
+     */
+    fun parseModuleName(moduleName: String): URI =
+      when (moduleName) {
+        "-" -> VmUtils.REPL_TEXT_URI
+        else ->
+          // Don't use `IoUtils.toUri` here becaus we need to normalize `\` paths to `/` on Windows.
+          try {
+            if (IoUtils.isUriLike(moduleName)) URI(moduleName)
+            // Can't just use URI constructor, because URI(null, null, "C:/foo/bar", null) turns
+            // into `URI("C", null, "/foo/bar", null)`.
+            else if (IoUtils.isWindowsAbsolutePath(moduleName)) Path.of(moduleName).toUri()
+            else URI(null, null, IoUtils.toNormalizedPathString(Path.of(moduleName)), null)
+          } catch (e: URISyntaxException) {
+            val message = buildString {
+              append("Module URI `$moduleName` has invalid syntax (${e.reason}).")
+              if (e.index > -1) {
+                append("\n\n")
+                append(moduleName)
+                append("\n")
+                append(" ".repeat(e.index))
+                append("^")
+              }
+            }
+            throw CliException(message)
+          }
+      }
+  }
+
   private val defaults = CliBaseOptions()
 
   private val output =
@@ -114,7 +150,7 @@ class BaseOptions : OptionGroup() {
 
   val settings: URI? by
     option(names = arrayOf("--settings"), help = "Pkl settings module to use.").single().convert {
-      IoUtils.toUri(it)
+      parseModuleName(it)
     }
 
   val timeout: Duration? by
diff --git a/pkl-commons-cli/src/main/kotlin/org/pkl/commons/cli/commands/ModulesCommand.kt b/pkl-commons-cli/src/main/kotlin/org/pkl/commons/cli/commands/ModulesCommand.kt
index c19fe58c..b2c45c05 100644
--- a/pkl-commons-cli/src/main/kotlin/org/pkl/commons/cli/commands/ModulesCommand.kt
+++ b/pkl-commons-cli/src/main/kotlin/org/pkl/commons/cli/commands/ModulesCommand.kt
@@ -29,7 +29,7 @@ abstract class ModulesCommand(name: String, helpLink: String, help: String = "")
   ) {
   open val modules: List<URI> by
     argument(name = "<modules>", help = "Module paths or URIs to evaluate.")
-      .convert { parseModuleName(it) }
+      .convert { BaseOptions.parseModuleName(it) }
       .multiple(required = true)
 
   protected val projectOptions by ProjectOptions()
diff --git a/pkl-commons-test/pkl-commons-test.gradle.kts b/pkl-commons-test/pkl-commons-test.gradle.kts
index 80a5394b..fc3e40b0 100644
--- a/pkl-commons-test/pkl-commons-test.gradle.kts
+++ b/pkl-commons-test/pkl-commons-test.gradle.kts
@@ -58,6 +58,11 @@ for (packageDir in file("src/main/files/packages").listFiles()!!) {
     }
     doLast {
       val outputFile = destinationDir.get().asFile.resolve("${packageDir.name}.json")
+      if (buildInfo.os.isWindows) {
+        val contents = outputFile.readText()
+        // workaround for https://github.com/gradle/gradle/issues/1151
+        outputFile.writeText(contents.replace("\r\n", "\n"))
+      }
       shasumFile.get().asFile.writeText(outputFile.computeChecksum())
     }
   }
diff --git a/pkl-commons-test/src/main/kotlin/org/pkl/commons/test/InputOutputTestEngine.kt b/pkl-commons-test/src/main/kotlin/org/pkl/commons/test/InputOutputTestEngine.kt
index 9366a500..4c7a864d 100644
--- a/pkl-commons-test/src/main/kotlin/org/pkl/commons/test/InputOutputTestEngine.kt
+++ b/pkl-commons-test/src/main/kotlin/org/pkl/commons/test/InputOutputTestEngine.kt
@@ -31,6 +31,7 @@ import org.junit.platform.engine.support.hierarchical.EngineExecutionContext
 import org.junit.platform.engine.support.hierarchical.HierarchicalTestEngine
 import org.junit.platform.engine.support.hierarchical.Node
 import org.junit.platform.engine.support.hierarchical.Node.DynamicTestExecutor
+import org.pkl.commons.toNormalizedPathString
 
 abstract class InputOutputTestEngine :
   HierarchicalTestEngine<InputOutputTestEngine.ExecutionContext>() {
@@ -106,7 +107,7 @@ abstract class InputOutputTestEngine :
   ): TestDescriptor {
     dirNode.inputDir.useDirectoryEntries { children ->
       for (child in children) {
-        val testPath = child.toString()
+        val testPath = child.toNormalizedPathString()
         val testName = child.fileName.toString()
         if (child.isRegularFile()) {
           if (
diff --git a/pkl-commons/src/main/kotlin/org/pkl/commons/Paths.kt b/pkl-commons/src/main/kotlin/org/pkl/commons/Paths.kt
index f2c0723a..8f95c922 100644
--- a/pkl-commons/src/main/kotlin/org/pkl/commons/Paths.kt
+++ b/pkl-commons/src/main/kotlin/org/pkl/commons/Paths.kt
@@ -71,3 +71,13 @@ fun Path.deleteRecursively() {
     walk().use { paths -> paths.sorted(Comparator.reverseOrder()).forEach { it.deleteIfExists() } }
   }
 }
+
+private val isWindows by lazy { System.getProperty("os.name").contains("Windows") }
+
+/** Copy implementation from IoUtils.toNormalizedPathString */
+fun Path.toNormalizedPathString(): String {
+  if (isWindows) {
+    return toString().replace("\\", "/")
+  }
+  return toString()
+}
diff --git a/pkl-commons/src/main/kotlin/org/pkl/commons/Strings.kt b/pkl-commons/src/main/kotlin/org/pkl/commons/Strings.kt
index cfe684d6..9adc4b0c 100644
--- a/pkl-commons/src/main/kotlin/org/pkl/commons/Strings.kt
+++ b/pkl-commons/src/main/kotlin/org/pkl/commons/Strings.kt
@@ -15,15 +15,24 @@
  */
 package org.pkl.commons
 
+import java.io.File
 import java.net.URI
 import java.nio.file.Path
+import java.util.regex.Pattern
 
 fun String.toPath(): Path = Path.of(this)
 
+private val uriLike = Pattern.compile("\\w+:[^\\\\].*")
+
+private val windowsPathLike = Pattern.compile("\\w:\\\\.*")
+
 /** Copy of org.pkl.core.util.IoUtils.toUri */
-fun String.toUri(): URI =
-  if (contains(":")) {
-    URI(this)
-  } else {
-    URI(null, null, this, null)
+fun String.toUri(): URI {
+  if (uriLike.matcher(this).matches()) {
+    return URI(this)
   }
+  if (windowsPathLike.matcher(this).matches()) {
+    return File(this).toURI()
+  }
+  return URI(null, null, this, null)
+}
diff --git a/pkl-core/pkl-core.gradle.kts b/pkl-core/pkl-core.gradle.kts
index 826cebe8..12b6425b 100644
--- a/pkl-core/pkl-core.gradle.kts
+++ b/pkl-core/pkl-core.gradle.kts
@@ -267,6 +267,21 @@ val testAlpineExecutableAmd64 by tasks.registering(Test::class) {
   }
 }
 
+val testWindowsExecutableAmd64 by tasks.registering(Test::class) {
+  dependsOn(":pkl-cli:windowsExecutableAmd64")
+
+  inputs.dir("src/test/files/LanguageSnippetTests/input")
+  inputs.dir("src/test/files/LanguageSnippetTests/input-helper")
+  inputs.dir("src/test/files/LanguageSnippetTests/output")
+
+  testClassesDirs = files(tasks.test.get().testClassesDirs)
+  classpath = tasks.test.get().classpath
+
+  useJUnitPlatform {
+    includeEngines("WindowsLanguageSnippetTestsEngine")
+  }
+}
+
 tasks.testNative {
   when {
     buildInfo.os.isMacOsX -> {
@@ -284,6 +299,9 @@ tasks.testNative {
         dependsOn(testAlpineExecutableAmd64)
       }
     }
+    buildInfo.os.isWindows -> {
+      dependsOn(testWindowsExecutableAmd64)
+    }
   }
 }
 
diff --git a/pkl-core/src/main/java/org/pkl/core/Platform.java b/pkl-core/src/main/java/org/pkl/core/Platform.java
index 38bd0dae..30eb3309 100644
--- a/pkl-core/src/main/java/org/pkl/core/Platform.java
+++ b/pkl-core/src/main/java/org/pkl/core/Platform.java
@@ -31,6 +31,7 @@ public final class Platform {
     var pklVersion = Release.current().version().toString();
     var osName = System.getProperty("os.name");
     if (osName.equals("Mac OS X")) osName = "macOS";
+    if (osName.contains("Windows")) osName = "Windows";
     var osVersion = System.getProperty("os.version");
     var architecture = System.getProperty("os.arch");
 
diff --git a/pkl-core/src/main/java/org/pkl/core/Release.java b/pkl-core/src/main/java/org/pkl/core/Release.java
index ede7c53f..4a479ac1 100644
--- a/pkl-core/src/main/java/org/pkl/core/Release.java
+++ b/pkl-core/src/main/java/org/pkl/core/Release.java
@@ -49,6 +49,7 @@ public final class Release {
     var commitId = properties.getProperty("commitId");
     var osName = System.getProperty("os.name");
     if (osName.equals("Mac OS X")) osName = "macOS";
+    if (osName.contains("Windows")) osName = "Windows";
     var osVersion = System.getProperty("os.version");
     var os = osName + " " + osVersion;
     var flavor = TruffleOptions.AOT ? "native" : "Java " + System.getProperty("java.version");
diff --git a/pkl-core/src/main/java/org/pkl/core/ast/builder/AstBuilder.java b/pkl-core/src/main/java/org/pkl/core/ast/builder/AstBuilder.java
index c4d15a7e..bf44cf44 100644
--- a/pkl-core/src/main/java/org/pkl/core/ast/builder/AstBuilder.java
+++ b/pkl-core/src/main/java/org/pkl/core/ast/builder/AstBuilder.java
@@ -1794,10 +1794,17 @@ public final class AstBuilder extends AbstractAstBuilder<Object> {
     try {
       resolvedUri = IoUtils.resolve(context.getSecurityManager(), moduleKey, parsedUri);
     } catch (FileNotFoundException e) {
-      throw exceptionBuilder()
-          .evalError("cannotFindModule", importUri)
-          .withSourceSection(createSourceSection(importUriCtx))
-          .build();
+
+      var exceptionBuilder =
+          exceptionBuilder()
+              .evalError("cannotFindModule", importUri)
+              .withSourceSection(createSourceSection(importUriCtx));
+      var path = parsedUri.getPath();
+      if (path != null && path.contains("\\")) {
+        exceptionBuilder.withHint(
+            "To resolve modules in nested directories, use `/` as the directory separator.");
+      }
+      throw exceptionBuilder.build();
     } catch (URISyntaxException e) {
       throw exceptionBuilder()
           .evalError("invalidModuleUri", importUri)
diff --git a/pkl-core/src/main/java/org/pkl/core/module/ModuleKeyFactories.java b/pkl-core/src/main/java/org/pkl/core/module/ModuleKeyFactories.java
index d02823b1..f26816ef 100644
--- a/pkl-core/src/main/java/org/pkl/core/module/ModuleKeyFactories.java
+++ b/pkl-core/src/main/java/org/pkl/core/module/ModuleKeyFactories.java
@@ -18,8 +18,8 @@ package org.pkl.core.module;
 import java.net.URI;
 import java.net.URISyntaxException;
 import java.nio.file.FileSystemNotFoundException;
-import java.nio.file.Path;
 import java.nio.file.Paths;
+import java.nio.file.spi.FileSystemProvider;
 import java.util.ArrayList;
 import java.util.Collections;
 import java.util.List;
@@ -141,15 +141,20 @@ public final class ModuleKeyFactories {
   private static class File implements ModuleKeyFactory {
     @Override
     public Optional<ModuleKey> create(URI uri) {
-      Path path;
-      try {
-        path = Path.of(uri);
-      } catch (FileSystemNotFoundException | IllegalArgumentException e) {
-        // none of the installed file system providers can handle this URI
+      // skip loading providers if the scheme is `file`.
+      if (uri.getScheme().equalsIgnoreCase("file")) {
+        return Optional.of(ModuleKeys.file(uri));
+      }
+      // don't handle jar-file URIs (these are handled by GenericUrl).
+      if (uri.getScheme().equalsIgnoreCase("jar")) {
         return Optional.empty();
       }
-
-      return Optional.of(ModuleKeys.file(uri, path));
+      for (FileSystemProvider provider : FileSystemProvider.installedProviders()) {
+        if (provider.getScheme().equalsIgnoreCase(uri.getScheme())) {
+          return Optional.of(ModuleKeys.file(uri));
+        }
+      }
+      return Optional.empty();
     }
   }
 
diff --git a/pkl-core/src/main/java/org/pkl/core/module/ModuleKeys.java b/pkl-core/src/main/java/org/pkl/core/module/ModuleKeys.java
index 48f0ddbd..60f6cb8c 100644
--- a/pkl-core/src/main/java/org/pkl/core/module/ModuleKeys.java
+++ b/pkl-core/src/main/java/org/pkl/core/module/ModuleKeys.java
@@ -16,9 +16,11 @@
 package org.pkl.core.module;
 
 import com.oracle.truffle.api.CompilerDirectives.TruffleBoundary;
+import java.io.File;
 import java.io.FileNotFoundException;
 import java.io.IOException;
 import java.io.InputStream;
+import java.net.JarURLConnection;
 import java.net.URI;
 import java.net.URISyntaxException;
 import java.net.http.HttpRequest;
@@ -88,8 +90,8 @@ public final class ModuleKeys {
   }
 
   /** Creates a module key for a {@code file:} module. */
-  public static ModuleKey file(URI uri, Path path) {
-    return new File(uri, path);
+  public static ModuleKey file(URI uri) {
+    return new File(uri);
   }
 
   /**
@@ -290,12 +292,10 @@ public final class ModuleKeys {
 
   private static class File extends DependencyAwareModuleKey {
     final URI uri;
-    final Path path;
 
-    File(URI uri, Path path) {
+    File(URI uri) {
       super(uri);
       this.uri = uri;
-      this.path = path;
     }
 
     @Override
@@ -316,7 +316,13 @@ public final class ModuleKeys {
     public ResolvedModuleKey resolve(SecurityManager securityManager)
         throws IOException, SecurityManagerException {
       securityManager.checkResolveModule(uri);
-      var realPath = path.toRealPath();
+      // Disallow paths that contain `\\` characters if on Windows
+      // (require `/` as the path separator on all OSes)
+      var uriPath = uri.getPath();
+      if (java.io.File.separatorChar == '\\' && uriPath != null && uriPath.contains("\\")) {
+        throw new FileNotFoundException();
+      }
+      var realPath = Path.of(uri).toRealPath();
       var resolvedUri = realPath.toUri();
       securityManager.checkResolveModule(resolvedUri);
       return ResolvedModuleKeys.file(this, resolvedUri, realPath);
@@ -325,7 +331,7 @@ public final class ModuleKeys {
     @Override
     protected Map<String, ? extends Dependency> getDependencies() {
       var projectDepsManager = VmContext.get(null).getProjectDependenciesManager();
-      if (projectDepsManager == null || !projectDepsManager.hasPath(path)) {
+      if (projectDepsManager == null || !projectDepsManager.hasPath(Path.of(uri))) {
         throw new PackageLoadError("cannotResolveDependencyNoProject");
       }
       return projectDepsManager.getDependencies();
@@ -519,6 +525,12 @@ public final class ModuleKeys {
       var url = IoUtils.toUrl(uri);
       var conn = url.openConnection();
       conn.connect();
+      if (conn instanceof JarURLConnection && IoUtils.isWindows()) {
+        // On Windows, opening a JarURLConnection prevents the jar file from being deleted, unless
+        // cacheing is disabled.
+        // See https://bugs.openjdk.org/browse/JDK-8239054
+        conn.setUseCaches(false);
+      }
       try (InputStream stream = conn.getInputStream()) {
         URI redirected;
         try {
diff --git a/pkl-core/src/main/java/org/pkl/core/module/ModulePathResolver.java b/pkl-core/src/main/java/org/pkl/core/module/ModulePathResolver.java
index 47a0eb77..d2265c5d 100644
--- a/pkl-core/src/main/java/org/pkl/core/module/ModulePathResolver.java
+++ b/pkl-core/src/main/java/org/pkl/core/module/ModulePathResolver.java
@@ -30,6 +30,7 @@ import java.util.Map;
 import javax.annotation.concurrent.GuardedBy;
 import org.pkl.core.module.PathElement.TreePathElement;
 import org.pkl.core.runtime.FileSystemManager;
+import org.pkl.core.util.IoUtils;
 import org.pkl.core.util.LateInit;
 
 /**
@@ -152,8 +153,8 @@ public final class ModulePathResolver implements AutoCloseable {
       // in case of duplicate path, first entry wins (cf. class loader)
       stream.forEach(
           (path) -> {
-            var relativized = basePath.relativize(path);
-            fileCache.putIfAbsent(relativized.toString(), path);
+            var relativized = IoUtils.relativize(path, basePath);
+            fileCache.putIfAbsent(IoUtils.toNormalizedPathString(relativized), path);
             var element = cachedPathElementRoot;
             for (var i = 0; i < relativized.getNameCount(); i++) {
               var name = relativized.getName(i).toString();
diff --git a/pkl-core/src/main/java/org/pkl/core/module/ProjectDependenciesManager.java b/pkl-core/src/main/java/org/pkl/core/module/ProjectDependenciesManager.java
index b07ee29d..633ee277 100644
--- a/pkl-core/src/main/java/org/pkl/core/module/ProjectDependenciesManager.java
+++ b/pkl-core/src/main/java/org/pkl/core/module/ProjectDependenciesManager.java
@@ -207,13 +207,15 @@ public final class ProjectDependenciesManager {
       if (projectDeps == null) {
         var depsPath = getProjectDepsFile();
         if (!Files.exists(depsPath)) {
-          throw new VmExceptionBuilder().evalError("missingProjectDepsJson", projectDir).build();
+          throw new VmExceptionBuilder()
+              .evalError("missingProjectDepsJson", projectDir.toUri())
+              .build();
         }
         try {
           projectDeps = ProjectDeps.parse(depsPath);
         } catch (IOException | URISyntaxException | JsonParseException e) {
           throw new VmExceptionBuilder()
-              .evalError("invalidProjectDepsJson", depsPath, e.getMessage())
+              .evalError("invalidProjectDepsJson", depsPath.toUri(), e.getMessage())
               .withCause(e)
               .build();
         }
diff --git a/pkl-core/src/main/java/org/pkl/core/module/ResolvedModuleKeys.java b/pkl-core/src/main/java/org/pkl/core/module/ResolvedModuleKeys.java
index 647bd9c3..8fcaaa96 100644
--- a/pkl-core/src/main/java/org/pkl/core/module/ResolvedModuleKeys.java
+++ b/pkl-core/src/main/java/org/pkl/core/module/ResolvedModuleKeys.java
@@ -15,10 +15,12 @@
  */
 package org.pkl.core.module;
 
+import java.io.File;
 import java.io.IOException;
 import java.net.URI;
 import java.net.URL;
 import java.nio.charset.StandardCharsets;
+import java.nio.file.AccessDeniedException;
 import java.nio.file.Files;
 import java.nio.file.Path;
 import org.pkl.core.util.IoUtils;
@@ -75,7 +77,16 @@ public final class ResolvedModuleKeys {
 
     @Override
     public String loadSource() throws IOException {
-      return Files.readString(path, StandardCharsets.UTF_8);
+      try {
+        return Files.readString(path, StandardCharsets.UTF_8);
+      } catch (AccessDeniedException e) {
+        // Windows throws `AccessDeniedException` when reading directories.
+        // Sync error between different OSes.
+        if (Files.isDirectory(path)) {
+          throw new IOException("Is a directory");
+        }
+        throw e;
+      }
     }
   }
 
diff --git a/pkl-core/src/main/java/org/pkl/core/packages/Dependency.java b/pkl-core/src/main/java/org/pkl/core/packages/Dependency.java
index 2fe41448..991462a9 100644
--- a/pkl-core/src/main/java/org/pkl/core/packages/Dependency.java
+++ b/pkl-core/src/main/java/org/pkl/core/packages/Dependency.java
@@ -50,7 +50,7 @@ public abstract class Dependency {
 
     public Path resolveAssetPath(Path projectDir, PackageAssetUri packageAssetUri) {
       // drop 1 to remove leading `/`
-      var assetPath = packageAssetUri.getAssetPath().toString().substring(1);
+      var assetPath = packageAssetUri.getAssetPath().substring(1);
       return projectDir.resolve(path).resolve(assetPath);
     }
 
diff --git a/pkl-core/src/main/java/org/pkl/core/packages/PackageAssetUri.java b/pkl-core/src/main/java/org/pkl/core/packages/PackageAssetUri.java
index 6e52146b..ed6ce589 100644
--- a/pkl-core/src/main/java/org/pkl/core/packages/PackageAssetUri.java
+++ b/pkl-core/src/main/java/org/pkl/core/packages/PackageAssetUri.java
@@ -20,6 +20,7 @@ import java.net.URISyntaxException;
 import java.nio.file.Path;
 import org.pkl.core.Version;
 import org.pkl.core.util.ErrorMessages;
+import org.pkl.core.util.IoUtils;
 
 /**
  * The canonical URI of an asset within a package, i.e., a package URI with a fragment path. For
@@ -28,7 +29,7 @@ import org.pkl.core.util.ErrorMessages;
 public final class PackageAssetUri {
   private final URI uri;
   private final PackageUri packageUri;
-  private final Path assetPath;
+  private final String assetPath;
 
   public static PackageAssetUri create(URI uri) {
     try {
@@ -41,7 +42,7 @@ public final class PackageAssetUri {
   public PackageAssetUri(PackageUri packageUri, String assetPath) {
     this.uri = packageUri.getUri().resolve("#" + assetPath);
     this.packageUri = packageUri;
-    this.assetPath = Path.of(assetPath);
+    this.assetPath = assetPath;
   }
 
   public PackageAssetUri(String uri) throws URISyntaxException {
@@ -60,7 +61,7 @@ public final class PackageAssetUri {
       throw new URISyntaxException(
           uri.toString(), ErrorMessages.create("cannotHaveRelativeFragment", fragment, uri));
     }
-    this.assetPath = Path.of(fragment);
+    this.assetPath = fragment;
   }
 
   public URI getUri() {
@@ -71,7 +72,7 @@ public final class PackageAssetUri {
     return packageUri;
   }
 
-  public Path getAssetPath() {
+  public String getAssetPath() {
     return assetPath;
   }
 
@@ -102,6 +103,7 @@ public final class PackageAssetUri {
   }
 
   public PackageAssetUri resolve(String path) {
-    return new PackageAssetUri(packageUri, assetPath.resolve(path).toString());
+    var resolvedPath = IoUtils.toNormalizedPathString(Path.of(assetPath).resolve(path));
+    return new PackageAssetUri(packageUri, resolvedPath);
   }
 }
diff --git a/pkl-core/src/main/java/org/pkl/core/packages/PackageResolvers.java b/pkl-core/src/main/java/org/pkl/core/packages/PackageResolvers.java
index dbc3fd49..fbf3d085 100644
--- a/pkl-core/src/main/java/org/pkl/core/packages/PackageResolvers.java
+++ b/pkl-core/src/main/java/org/pkl/core/packages/PackageResolvers.java
@@ -335,8 +335,7 @@ final class PackageResolvers {
       var entries = cachedEntries.get(packageUri);
       // need to normalize here but not in `doListElments` nor `doHasElement` because
       // `TreePathElement.getElement` does normalization already.
-      var path = uri.getAssetPath().normalize().toString();
-      assert path.startsWith("/");
+      var path = IoUtils.toNormalizedPathString(Path.of(uri.getAssetPath()).normalize());
       return entries.get(path).array();
     }
 
@@ -496,7 +495,9 @@ final class PackageResolvers {
         downloadMetadata(packageUri, requestUri, tmpPath, checksums);
         Files.createDirectories(cachePath.getParent());
         Files.move(tmpPath, cachePath, StandardCopyOption.ATOMIC_MOVE);
-        Files.setPosixFilePermissions(cachePath, FILE_PERMISSIONS);
+        if (!IoUtils.isWindows()) {
+          Files.setPosixFilePermissions(cachePath, FILE_PERMISSIONS);
+        }
         return cachePath;
       } finally {
         Files.deleteIfExists(tmpPath);
@@ -545,7 +546,9 @@ final class PackageResolvers {
         verifyPackageZipBytes(packageUri, dependencyMetadata, checksumBytes);
         Files.createDirectories(cachePath.getParent());
         Files.move(tmpPath, cachePath, StandardCopyOption.ATOMIC_MOVE);
-        Files.setPosixFilePermissions(cachePath, FILE_PERMISSIONS);
+        if (!IoUtils.isWindows()) {
+          Files.setPosixFilePermissions(cachePath, FILE_PERMISSIONS);
+        }
         return cachePath;
       } finally {
         Files.deleteIfExists(tmpPath);
diff --git a/pkl-core/src/main/java/org/pkl/core/project/ProjectDependenciesResolver.java b/pkl-core/src/main/java/org/pkl/core/project/ProjectDependenciesResolver.java
index d37f3c7f..f528f84b 100644
--- a/pkl-core/src/main/java/org/pkl/core/project/ProjectDependenciesResolver.java
+++ b/pkl-core/src/main/java/org/pkl/core/project/ProjectDependenciesResolver.java
@@ -33,6 +33,7 @@ import org.pkl.core.packages.PackageUri;
 import org.pkl.core.util.EconomicMaps;
 import org.pkl.core.util.EconomicSets;
 import org.pkl.core.util.ErrorMessages;
+import org.pkl.core.util.IoUtils;
 import org.pkl.core.util.Nullable;
 
 /**
@@ -78,7 +79,7 @@ public final class ProjectDependenciesResolver {
 
   private void log(String message) {
     try {
-      logWriter.write(message + "\n");
+      logWriter.write(message + IoUtils.getLineSeparator());
     } catch (IOException e) {
       throw new UncheckedIOException(e);
     }
@@ -130,7 +131,7 @@ public final class ProjectDependenciesResolver {
     var packageUri = declaredDependencies.getMyPackageUri();
     assert packageUri != null;
     var projectDir = Path.of(declaredDependencies.getProjectFileUri()).getParent();
-    var relativePath = this.project.getProjectDir().relativize(projectDir);
+    var relativePath = IoUtils.relativize(projectDir, this.project.getProjectDir());
     var localDependency = new LocalDependency(packageUri.toProjectPackageUri(), relativePath);
     updateDependency(localDependency);
     buildResolvedDependencies(declaredDependencies);
diff --git a/pkl-core/src/main/java/org/pkl/core/project/ProjectDeps.java b/pkl-core/src/main/java/org/pkl/core/project/ProjectDeps.java
index d5b61b59..be18cac8 100644
--- a/pkl-core/src/main/java/org/pkl/core/project/ProjectDeps.java
+++ b/pkl-core/src/main/java/org/pkl/core/project/ProjectDeps.java
@@ -35,6 +35,7 @@ import org.pkl.core.packages.PackageLoadError;
 import org.pkl.core.packages.PackageUtils;
 import org.pkl.core.runtime.VmExceptionBuilder;
 import org.pkl.core.util.EconomicMaps;
+import org.pkl.core.util.IoUtils;
 import org.pkl.core.util.Nullable;
 import org.pkl.core.util.json.Json;
 import org.pkl.core.util.json.Json.FormatException;
@@ -196,7 +197,7 @@ public final class ProjectDeps {
       jsonWriter.beginObject();
       jsonWriter.name("type").value("local");
       jsonWriter.name("uri").value(localDependency.getPackageUri().toString());
-      jsonWriter.name("path").value(localDependency.getPath().toString());
+      jsonWriter.name("path").value(IoUtils.toNormalizedPathString(localDependency.getPath()));
       jsonWriter.endObject();
     }
 
diff --git a/pkl-core/src/main/java/org/pkl/core/project/ProjectPackager.java b/pkl-core/src/main/java/org/pkl/core/project/ProjectPackager.java
index f1bffab3..28492eae 100644
--- a/pkl-core/src/main/java/org/pkl/core/project/ProjectPackager.java
+++ b/pkl-core/src/main/java/org/pkl/core/project/ProjectPackager.java
@@ -20,6 +20,8 @@ import java.io.IOException;
 import java.io.OutputStream;
 import java.io.UncheckedIOException;
 import java.io.Writer;
+import java.net.URI;
+import java.net.URISyntaxException;
 import java.nio.file.Files;
 import java.nio.file.Path;
 import java.security.DigestOutputStream;
@@ -119,13 +121,18 @@ public final class ProjectPackager {
     this.outputWriter = outputWriter;
   }
 
+  private void writeLine(String line) throws IOException {
+    outputWriter.write(line);
+    outputWriter.write(IoUtils.getLineSeparator());
+  }
+
   public void createPackages() throws IOException {
     for (var project : projects) {
       var packageResult = doPackage(project);
-      outputWriter.write(workingDir.relativize(packageResult.getMetadataFile()) + "\n");
-      outputWriter.write(workingDir.relativize(packageResult.getMetadataChecksumFile()) + "\n");
-      outputWriter.write(workingDir.relativize(packageResult.getZipFile()) + "\n");
-      outputWriter.write(workingDir.relativize(packageResult.getZipChecksumFile()) + "\n");
+      writeLine(IoUtils.relativize(packageResult.getMetadataFile(), workingDir).toString());
+      writeLine(IoUtils.relativize(packageResult.getMetadataChecksumFile(), workingDir).toString());
+      writeLine(IoUtils.relativize(packageResult.getZipFile(), workingDir).toString());
+      writeLine(IoUtils.relativize(packageResult.getZipChecksumFile(), workingDir).toString());
       outputWriter.flush();
     }
   }
@@ -302,8 +309,8 @@ public final class ProjectPackager {
     }
     try (var zos = new ZipOutputStream(digestOutputStream)) {
       for (var file : files) {
-        var relativePath = project.getProjectDir().relativize(file);
-        var zipEntry = new ZipEntry(relativePath.toString());
+        var relativePath = IoUtils.relativize(file, project.getProjectDir());
+        var zipEntry = new ZipEntry(IoUtils.toNormalizedPathString(relativePath));
         zipEntry.setTimeLocal(ZIP_ENTRY_MTIME);
         zos.putNextEntry(zipEntry);
         Files.copy(file, zos);
@@ -342,8 +349,8 @@ public final class ProjectPackager {
           .filter(Files::isRegularFile)
           .filter(
               (it) -> {
-                var fileNameRelativeToProjectRoot =
-                    project.getProjectDir().relativize(it).toString();
+                var relativePath = IoUtils.relativize(it, project.getProjectDir());
+                var fileNameRelativeToProjectRoot = IoUtils.toNormalizedPathString(relativePath);
                 for (var pattern : excludePatterns) {
                   if (pattern.matcher(it.getFileName().toString()).matches()) {
                     return false;
@@ -363,7 +370,7 @@ public final class ProjectPackager {
   }
 
   private boolean isAbsoluteImport(String importStr) {
-    return importStr.matches("\\w:.*") || importStr.startsWith("@");
+    return importStr.matches("\\w+:.*") || importStr.startsWith("@");
   }
 
   /**
@@ -386,8 +393,17 @@ public final class ProjectPackager {
       if (isAbsoluteImport(importStr)) {
         continue;
       }
-      var importPath = Path.of(importStr);
-      if (importPath.isAbsolute() && !project.getProjectDir().toString().equals("/")) {
+      URI importUri;
+      try {
+        importUri = IoUtils.toUri(importStr);
+      } catch (URISyntaxException e) {
+        throw new VmExceptionBuilder()
+            .evalError("invalidModuleUri", importStr)
+            .withSourceSection(sourceSection)
+            .build()
+            .toPklException(stackFrameTransformer);
+      }
+      if (importStr.startsWith("/") && !project.getProjectDir().toString().equals("/")) {
         throw new VmExceptionBuilder()
             .evalError("invalidRelativeProjectImport", importStr)
             .withSourceSection(sourceSection)
@@ -395,6 +411,7 @@ public final class ProjectPackager {
             .toPklException(stackFrameTransformer);
       }
       var currentPath = pklModulePath.getParent();
+      var importPath = Path.of(importUri.getPath());
       // It's not good enough to just check the normalized path to see whether it exists within the
       // root dir.
       // It's possible that the import path resolves to a path outside the project dir,
@@ -416,7 +433,7 @@ public final class ProjectPackager {
 
   private @Nullable List<Pair<String, SourceSection>> getImportsAndReads(Path pklModulePath) {
     try {
-      var moduleKey = ModuleKeys.file(pklModulePath.toUri(), pklModulePath);
+      var moduleKey = ModuleKeys.file(pklModulePath.toUri());
       var resolvedModuleKey = ResolvedModuleKeys.file(moduleKey, moduleKey.getUri(), pklModulePath);
       return ImportsAndReadsParser.parse(moduleKey, resolvedModuleKey);
     } catch (IOException e) {
diff --git a/pkl-core/src/main/java/org/pkl/core/runtime/ModuleCache.java b/pkl-core/src/main/java/org/pkl/core/runtime/ModuleCache.java
index f01f350f..5558246b 100644
--- a/pkl-core/src/main/java/org/pkl/core/runtime/ModuleCache.java
+++ b/pkl-core/src/main/java/org/pkl/core/runtime/ModuleCache.java
@@ -195,10 +195,16 @@ public final class ModuleCache {
     } catch (SecurityManagerException | PackageLoadError e) {
       throw new VmExceptionBuilder().withOptionalLocation(importNode).withCause(e).build();
     } catch (FileNotFoundException | NoSuchFileException e) {
-      throw new VmExceptionBuilder()
-          .withOptionalLocation(importNode)
-          .evalError("cannotFindModule", module.getUri())
-          .build();
+      var exceptionBuilder =
+          new VmExceptionBuilder()
+              .withOptionalLocation(importNode)
+              .evalError("cannotFindModule", module.getUri());
+      var path = module.getUri().getPath();
+      if (path != null && path.contains("\\")) {
+        exceptionBuilder.withHint(
+            "To resolve modules in nested directories, use `/` as the directory separator.");
+      }
+      throw exceptionBuilder.build();
     } catch (IOException e) {
       throw new VmExceptionBuilder()
           .withOptionalLocation(importNode)
diff --git a/pkl-core/src/main/java/org/pkl/core/util/IoUtils.java b/pkl-core/src/main/java/org/pkl/core/util/IoUtils.java
index a5da3df2..02359057 100644
--- a/pkl-core/src/main/java/org/pkl/core/util/IoUtils.java
+++ b/pkl-core/src/main/java/org/pkl/core/util/IoUtils.java
@@ -35,6 +35,7 @@ import java.util.regex.Pattern;
 import java.util.zip.ZipEntry;
 import java.util.zip.ZipOutputStream;
 import org.pkl.core.PklBugException;
+import org.pkl.core.Platform;
 import org.pkl.core.SecurityManager;
 import org.pkl.core.SecurityManagerException;
 import org.pkl.core.module.ModuleKey;
@@ -43,7 +44,10 @@ import org.pkl.core.runtime.VmExceptionBuilder;
 
 public final class IoUtils {
 
-  private static final Pattern uriLike = Pattern.compile("\\w+:.*");
+  // Don't match paths like `C:\`, which are drive letters on Windows.
+  private static final Pattern uriLike = Pattern.compile("\\w+:[^\\\\].*");
+
+  private static final Pattern windowsPathLike = Pattern.compile("\\w:\\\\.*");
 
   private IoUtils() {}
 
@@ -66,12 +70,20 @@ public final class IoUtils {
     return uriLike.matcher(str).matches();
   }
 
+  public static boolean isWindowsAbsolutePath(String str) {
+    if (!isWindows()) return false;
+    return windowsPathLike.matcher(str).matches();
+  }
+
   /**
    * Converts the given string to a {@link URI}. This method MUST be used for constructing module
    * and resource URIs. Unlike {@code new URI(str)}, it correctly escapes paths of relative URIs.
    */
   public static URI toUri(String str) throws URISyntaxException {
-    return isUriLike(str) ? new URI(str) : new URI(null, null, str, null);
+    if (isUriLike(str)) {
+      return new URI(str);
+    }
+    return new URI(null, null, str, null);
   }
 
   /** Like {@link #toUri(String)}, except without checked exceptions. */
@@ -150,7 +162,8 @@ public final class IoUtils {
           new SimpleFileVisitor<>() {
             public FileVisitResult visitFile(Path file, BasicFileAttributes attrs)
                 throws IOException {
-              zipStream.putNextEntry(new ZipEntry(sourceDir.relativize(file).toString()));
+              var relativePath = relativize(file, sourceDir);
+              zipStream.putNextEntry(new ZipEntry(toNormalizedPathString(relativePath)));
               Files.copy(file, zipStream);
               zipStream.closeEntry();
               return FileVisitResult.CONTINUE;
@@ -180,6 +193,10 @@ public final class IoUtils {
     return System.getProperty("line.separator");
   }
 
+  public static Boolean isWindows() {
+    return Platform.current().operatingSystem().name().equals("Windows");
+  }
+
   public static String getName(String path) {
     var lastSep = Math.max(path.lastIndexOf('/'), path.lastIndexOf('\\'));
     return path.substring(lastSep + 1);
@@ -362,7 +379,9 @@ public final class IoUtils {
     }
   }
 
-  // URI.relativize() won't construct relative paths containing ".."
+  // URI.relativize won't construct relative paths containing `..`.
+  // Can't use Path.relativize because certain URI characters will throw InvalidPathException
+  // on Windows.
   public static URI relativize(URI uri, URI base) {
     if (uri.isOpaque()
         || base.isOpaque()
@@ -370,19 +389,60 @@ public final class IoUtils {
         || !Objects.equals(uri.getAuthority(), base.getAuthority())) {
       return uri;
     }
-
-    var basePath = Path.of(base.getPath());
-    if (!base.getRawPath().endsWith("/")) basePath = basePath.getParent();
-    var resultPath = basePath.relativize(Path.of(uri.getPath()));
-
+    var uriPath = uri.normalize().getPath();
+    var basePath = base.normalize().getPath();
     try {
-      return new URI(
-          null, null, null, -1, resultPath.toString(), uri.getQuery(), uri.getFragment());
+      if (basePath.isEmpty()) {
+        return uri;
+      }
+      var uriParts = Arrays.asList(uriPath.split("/"));
+      var baseParts = Arrays.asList(basePath.split("/"));
+      if (!basePath.endsWith("/")) {
+        // strip the last path segment of the base uri, unless it ends in a slash. `/foo/bar.pkl` ->
+        // `/foo`
+        baseParts = baseParts.subList(0, baseParts.size() - 1);
+      }
+      if (uriParts.equals(baseParts)) {
+        return new URI(null, null, null, -1, "", uri.getQuery(), uri.getFragment());
+      }
+      var start = 0;
+      while (start < Math.min(uriParts.size(), baseParts.size())) {
+        if (!uriParts.get(start).equals(baseParts.get(start))) {
+          break;
+        }
+        start++;
+      }
+      var uriPartsRemaining = uriParts.subList(start, uriParts.size());
+      var basePartsRemainig = baseParts.subList(start, baseParts.size());
+      if (basePartsRemainig.isEmpty()) {
+        return new URI(
+            null,
+            null,
+            null,
+            -1,
+            String.join("/", uriPartsRemaining),
+            uri.getQuery(),
+            uri.getFragment());
+      }
+      var resultingPath =
+          "../".repeat(basePartsRemainig.size()) + String.join("/", uriPartsRemaining);
+      return new URI(null, null, null, -1, resultingPath, uri.getQuery(), uri.getFragment());
     } catch (URISyntaxException e) {
-      throw new IllegalArgumentException(e);
+      // Impossible; started from a valid URI to begin with.
+      throw PklBugException.unreachableCode();
     }
   }
 
+  // On Windows, `Path.relativize` will fail if the two paths have different roots.
+  public static Path relativize(Path path, Path base) {
+    if (isWindows()) {
+      if (path.isAbsolute() && base.isAbsolute() && !path.getRoot().equals(base.getRoot())) {
+        return path;
+      }
+    }
+    return base.relativize(path);
+  }
+
   public static boolean isWhitespace(String str) {
     return str.codePoints().allMatch(Character::isWhitespace);
   }
@@ -597,6 +657,63 @@ public final class IoUtils {
     return newUri;
   }
 
+  public static boolean isReservedFilenameChar(char character) {
+    if (isWindows()) {
+      return isReservedWindowsFilenameChar(character);
+    }
+    // posix; only NULL and `/` are reserved.
+    return character == 0 || character == '/';
+  }
+
+  /** Tells if this character cannot be used for filenames on Windows. */
+  public static boolean isReservedWindowsFilenameChar(char character) {
+    return switch (character) {
+      case 0,
+              1,
+              2,
+              3,
+              4,
+              5,
+              6,
+              7,
+              8,
+              9,
+              10,
+              11,
+              12,
+              13,
+              14,
+              15,
+              16,
+              17,
+              18,
+              19,
+              20,
+              21,
+              22,
+              23,
+              24,
+              25,
+              26,
+              27,
+              28,
+              29,
+              30,
+              31,
+              '<',
+              '>',
+              ':',
+              '"',
+              '\\',
+              '/',
+              '|',
+              '?',
+              '*' ->
+          true;
+      default -> false;
+    };
+  }
+
   /**
    * Windows reserves characters {@code <>:"\|?*} in filenames.
    *
@@ -608,19 +725,27 @@ public final class IoUtils {
     var sb = new StringBuilder();
     for (var i = 0; i < path.length(); i++) {
       var character = path.charAt(i);
-      switch (character) {
-        case '<', '>', ':', '"', '\\', '|', '?', '*' -> {
-          sb.append('(');
-          sb.append(ByteArrayUtils.toHex(new byte[] {(byte) character}));
-          sb.append(")");
-        }
-        case '(' -> sb.append("((");
-        default -> sb.append(path.charAt(i));
+      if (isReservedWindowsFilenameChar(character) && character != '/') {
+        sb.append('(');
+        sb.append(ByteArrayUtils.toHex(new byte[] {(byte) character}));
+        sb.append(")");
+      } else if (character == '(') {
+        sb.append("((");
+      } else {
+        sb.append(character);
       }
     }
     return sb.toString();
   }
 
+  /** Returns a path string that uses unix-like path separators. */
+  public static String toNormalizedPathString(Path path) {
+    if (isWindows()) {
+      return path.toString().replace("\\", "/");
+    }
+    return path.toString();
+  }
+
   private static int getExclamationMarkIndex(String jarUri) {
     var index = jarUri.indexOf('!');
     if (index == -1) {
diff --git a/pkl-core/src/test/files/LanguageSnippetTests/input/api/releaseModule.pkl b/pkl-core/src/test/files/LanguageSnippetTests/input/api/releaseModule.pkl
index 0ef1c390..8436992b 100644
--- a/pkl-core/src/test/files/LanguageSnippetTests/input/api/releaseModule.pkl
+++ b/pkl-core/src/test/files/LanguageSnippetTests/input/api/releaseModule.pkl
@@ -12,7 +12,7 @@ facts {
   }
 
   ["versionInfo"] {
-    current.versionInfo.contains("macOS") || current.versionInfo.contains("Linux")
+    current.versionInfo.contains("macOS") || current.versionInfo.contains("Linux") || current.versionInfo.contains("Windows")
   }
 
   ["commitId"] {
diff --git a/pkl-core/src/test/files/LanguageSnippetTests/input/errors/invalidImportBackslashSep.pkl b/pkl-core/src/test/files/LanguageSnippetTests/input/errors/invalidImportBackslashSep.pkl
new file mode 100644
index 00000000..82a3c4aa
--- /dev/null
+++ b/pkl-core/src/test/files/LanguageSnippetTests/input/errors/invalidImportBackslashSep.pkl
@@ -0,0 +1,2 @@
+// In all OSes, the directory separator is forward slash. 
+res = import(#"..\basic\baseModule.pkl"#)
diff --git a/pkl-core/src/test/files/LanguageSnippetTests/output/errors/invalidImportBackslashSep.err b/pkl-core/src/test/files/LanguageSnippetTests/output/errors/invalidImportBackslashSep.err
new file mode 100644
index 00000000..e4d36b97
--- /dev/null
+++ b/pkl-core/src/test/files/LanguageSnippetTests/output/errors/invalidImportBackslashSep.err
@@ -0,0 +1,12 @@
+–– Pkl Error ––
+Cannot find module `file:///$snippetsDir/input/errors/..%5Cbasic%5CbaseModule.pkl`.
+
+x | res = import(#"..\basic\baseModule.pkl"#)
+          ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
+at invalidImportBackslashSep#res (file:///$snippetsDir/input/errors/invalidImportBackslashSep.pkl)
+
+To resolve modules in nested directories, use `/` as the directory separator.
+
+xxx | text = renderer.renderDocument(value)
+             ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
+at pkl.base#Module.output.text (pkl:base)
diff --git a/pkl-core/src/test/files/LanguageSnippetTests/output/projects/badProjectDeps1/bug.err b/pkl-core/src/test/files/LanguageSnippetTests/output/projects/badProjectDeps1/bug.err
index fe03d702..2c21653e 100644
--- a/pkl-core/src/test/files/LanguageSnippetTests/output/projects/badProjectDeps1/bug.err
+++ b/pkl-core/src/test/files/LanguageSnippetTests/output/projects/badProjectDeps1/bug.err
@@ -1,5 +1,5 @@
 –– Pkl Error ––
-Cannot resolve dependency because file `/$snippetsDir/input/projects/badProjectDeps1/PklProject.deps.json` is malformed.
+Cannot resolve dependency because file `file:///$snippetsDir/input/projects/badProjectDeps1/PklProject.deps.json` is malformed.
 Run `pkl project resolve` to re-create this file.
 
 x | import "@bird/Bird.pkl"
diff --git a/pkl-core/src/test/files/LanguageSnippetTests/output/projects/badProjectDeps2/bug.err b/pkl-core/src/test/files/LanguageSnippetTests/output/projects/badProjectDeps2/bug.err
index 3d43f741..d42b59b7 100644
--- a/pkl-core/src/test/files/LanguageSnippetTests/output/projects/badProjectDeps2/bug.err
+++ b/pkl-core/src/test/files/LanguageSnippetTests/output/projects/badProjectDeps2/bug.err
@@ -1,5 +1,5 @@
 –– Pkl Error ––
-Cannot resolve dependency because file `/$snippetsDir/input/projects/badProjectDeps2/PklProject.deps.json` is malformed.
+Cannot resolve dependency because file `file:///$snippetsDir/input/projects/badProjectDeps2/PklProject.deps.json` is malformed.
 Run `pkl project resolve` to re-create this file.
 
 x | import "@bird/Bird.pkl"
diff --git a/pkl-core/src/test/files/LanguageSnippetTests/output/projects/missingProjectDeps/bug.err b/pkl-core/src/test/files/LanguageSnippetTests/output/projects/missingProjectDeps/bug.err
index f965f99b..679ecc06 100644
--- a/pkl-core/src/test/files/LanguageSnippetTests/output/projects/missingProjectDeps/bug.err
+++ b/pkl-core/src/test/files/LanguageSnippetTests/output/projects/missingProjectDeps/bug.err
@@ -1,5 +1,5 @@
 –– Pkl Error ––
-Cannot resolve dependency because file `PklProject.deps.json` is missing in project directory `/$snippetsDir/input/projects/missingProjectDeps`.
+Cannot resolve dependency because file `PklProject.deps.json` is missing in project directory `file:///$snippetsDir/input/projects/missingProjectDeps/`.
 
 x | import "@birds/Bird.pkl"
            ^^^^^^^^^^^^^^^^^
diff --git a/pkl-core/src/test/kotlin/org/pkl/core/EvaluatorTest.kt b/pkl-core/src/test/kotlin/org/pkl/core/EvaluatorTest.kt
index 0d6e1c4d..f0de9784 100644
--- a/pkl-core/src/test/kotlin/org/pkl/core/EvaluatorTest.kt
+++ b/pkl-core/src/test/kotlin/org/pkl/core/EvaluatorTest.kt
@@ -74,11 +74,12 @@ class EvaluatorTest {
 
   @Test
   fun `evaluate non-existing file`() {
+    val file = File("/non/existing")
     val e = assertThrows<PklException> {
-      evaluator.evaluate(file(File("/non/existing")))
+      evaluator.evaluate(file(file))
     }
     assertThat(e)
-      .hasMessageContaining("Cannot find module `file:///non/existing`.")
+      .hasMessageContaining("Cannot find module `${file.toPath().toUri()}`.")
   }
 
   @Test
@@ -92,13 +93,14 @@ class EvaluatorTest {
 
   @Test
   fun `evaluate non-existing path`() {
+    val path = "/non/existing".toPath()
     val e = assertThrows<PklException> {
-      evaluator.evaluate(path("/non/existing".toPath()))
+      evaluator.evaluate(path(path))
     }
     assertThat(e)
-      .hasMessageContaining("Cannot find module `file:///non/existing`.")
+      .hasMessageContaining("Cannot find module `${path.toUri()}`.")
   }
-  
+
   @Test
   fun `evaluate zip file system path`(@TempDir tempDir: Path) {
     val zipFile = createModulesZip(tempDir)
diff --git a/pkl-core/src/test/kotlin/org/pkl/core/LanguageSnippetTests.kt b/pkl-core/src/test/kotlin/org/pkl/core/LanguageSnippetTests.kt
index 5e5ac8af..1d2c788e 100644
--- a/pkl-core/src/test/kotlin/org/pkl/core/LanguageSnippetTests.kt
+++ b/pkl-core/src/test/kotlin/org/pkl/core/LanguageSnippetTests.kt
@@ -13,3 +13,6 @@ class LinuxLanguageSnippetTests
 
 @Testable
 class AlpineLanguageSnippetTests
+
+@Testable
+class WindowsLanguageSnippetTests
diff --git a/pkl-core/src/test/kotlin/org/pkl/core/LanguageSnippetTestsEngine.kt b/pkl-core/src/test/kotlin/org/pkl/core/LanguageSnippetTestsEngine.kt
index 516743b5..192bf0d7 100644
--- a/pkl-core/src/test/kotlin/org/pkl/core/LanguageSnippetTestsEngine.kt
+++ b/pkl-core/src/test/kotlin/org/pkl/core/LanguageSnippetTestsEngine.kt
@@ -51,7 +51,7 @@ abstract class AbstractLanguageSnippetTestsEngine : InputOutputTestEngine() {
     else parent?.getProjectDir()
 
   override fun expectedOutputFileFor(inputFile: Path): Path {
-    val relativePath = inputDir.relativize(inputFile).toString()
+    val relativePath = IoUtils.relativize(inputFile, inputDir).toString()
     val stdoutPath =
       if (relativePath.matches(hiddenExtensionRegex)) relativePath.dropLast(4)
       else relativePath.dropLast(3) + "pcf"
@@ -62,12 +62,12 @@ abstract class AbstractLanguageSnippetTestsEngine : InputOutputTestEngine() {
     // disable SHA verification for packages
     IoUtils.setTestMode()
   }
-  
+
   override fun afterAll() {
     packageServer.close()
   }
-  
-  protected fun String.stripFilePaths() = replace(snippetsDir.toString(), "/\$snippetsDir")
+
+  protected fun String.stripFilePaths() = replace(snippetsDir.toUri().toString(), "file:///\$snippetsDir/")
 
   protected fun String.stripLineNumbers() = replace(lineNumberRegex) { result ->
     // replace line number with equivalent number of 'x' characters to keep formatting intact
@@ -82,6 +82,11 @@ abstract class AbstractLanguageSnippetTestsEngine : InputOutputTestEngine() {
   
   protected fun String.stripStdlibLocationSha(): String =
     replace("https://github.com/apple/pkl/blob/${Release.current().commitId()}/stdlib/", "https://github.com/apple/pkl/blob/\$commitId/stdlib/")
+
+  protected fun String.withUnixLineEndings(): String {
+    return if (System.lineSeparator() == "\r\n") replace("\r\n", "\n")
+      else this
+  }
 }
 
 class LanguageSnippetTestsEngine : AbstractLanguageSnippetTestsEngine() {
@@ -143,7 +148,7 @@ class LanguageSnippetTestsEngine : AbstractLanguageSnippetTestsEngine() {
         .stripVersionCheckErrorMessage()
     }
 
-    val stderr = logWriter.toString()
+    val stderr = logWriter.toString().withUnixLineEndings()
 
     return (success && stderr.isBlank()) to (output + stderr).stripFilePaths().stripWebsite().stripStdlibLocationSha()
   }
@@ -216,7 +221,7 @@ abstract class AbstractNativeLanguageSnippetTestsEngine : AbstractLanguageSnippe
     val process = builder.start()
     return try {
       val (out, err) = listOf(process.inputStream, process.errorStream)
-        .map { it.reader().readText() }
+        .map { it.reader().readText().withUnixLineEndings() }
       val success = process.waitFor() == 0 && err.isBlank()
       success to (out + err)
         .stripFilePaths()
@@ -254,3 +259,8 @@ class AlpineLanguageSnippetTestsEngine : AbstractNativeLanguageSnippetTestsEngin
   override val pklExecutablePath: Path = rootProjectDir.resolve("pkl-cli/build/executable/pkl-alpine-linux-amd64")
   override val testClass: KClass<*> = AlpineLanguageSnippetTests::class
 }
+
+class WindowsLanguageSnippetTestsEngine : AbstractNativeLanguageSnippetTestsEngine() {
+  override val pklExecutablePath: Path = rootProjectDir.resolve("pkl-cli/build/executable/pkl-windows-amd64.exe")
+  override val testClass: KClass<*> = WindowsLanguageSnippetTests::class
+}
diff --git a/pkl-core/src/test/kotlin/org/pkl/core/SecurityManagersTest.kt b/pkl-core/src/test/kotlin/org/pkl/core/SecurityManagersTest.kt
index 9f79614a..62615879 100644
--- a/pkl-core/src/test/kotlin/org/pkl/core/SecurityManagersTest.kt
+++ b/pkl-core/src/test/kotlin/org/pkl/core/SecurityManagersTest.kt
@@ -181,11 +181,11 @@ class SecurityManagersTest {
       rootDir
     )
 
-    manager.checkResolveModule(URI("file:///foo/bar/baz.pkl"))
-    manager.checkReadResource(URI("file:///foo/bar/baz.pkl"))
+    manager.checkResolveModule(Path.of("/foo/bar/baz.pkl").toUri())
+    manager.checkReadResource(Path.of("/foo/bar/baz.pkl").toUri())
 
-    manager.checkResolveModule(URI("file:///foo/bar/qux/../baz.pkl"))
-    manager.checkReadResource(URI("file:///foo/bar/qux/../baz.pkl"))
+    manager.checkResolveModule(Path.of("/foo/bar/qux/../baz.pkl").toUri())
+    manager.checkReadResource(Path.of("/foo/bar/qux/../baz.pkl").toUri())
   }
 
   @Test
@@ -233,17 +233,17 @@ class SecurityManagersTest {
     )
 
     assertThrows<SecurityManagerException> {
-      manager.checkResolveModule(URI("file:///foo/baz.pkl"))
+      manager.checkResolveModule(Path.of("/foo/baz.pkl").toUri())
     }
     assertThrows<SecurityManagerException> {
-      manager.checkReadResource(URI("file:///foo/baz.pkl"))
+      manager.checkReadResource(Path.of("/foo/baz.pkl").toUri())
     }
 
     assertThrows<SecurityManagerException> {
-      manager.checkResolveModule(URI("file:///foo/bar/../baz.pkl"))
+      manager.checkResolveModule(Path.of("/foo/bar/../baz.pkl").toUri())
     }
     assertThrows<SecurityManagerException> {
-      manager.checkReadResource(URI("file:///foo/bar/../baz.pkl"))
+      manager.checkReadResource(Path.of("/foo/bar/../baz.pkl").toUri())
     }
   }
 }
diff --git a/pkl-core/src/test/kotlin/org/pkl/core/module/ModuleKeysTest.kt b/pkl-core/src/test/kotlin/org/pkl/core/module/ModuleKeysTest.kt
index 35297a4f..1056cd21 100644
--- a/pkl-core/src/test/kotlin/org/pkl/core/module/ModuleKeysTest.kt
+++ b/pkl-core/src/test/kotlin/org/pkl/core/module/ModuleKeysTest.kt
@@ -57,7 +57,7 @@ class ModuleKeysTest {
     file.writeString("age = 40")
 
     val uri = file.toUri()
-    val key = ModuleKeys.file(uri, file.toAbsolutePath())
+    val key = ModuleKeys.file(uri)
 
     assertThat(key.uri).isEqualTo(uri)
     assertThat(key.isCached).isTrue
diff --git a/pkl-core/src/test/kotlin/org/pkl/core/project/ProjectDependenciesResolverTest.kt b/pkl-core/src/test/kotlin/org/pkl/core/project/ProjectDependenciesResolverTest.kt
index ff6d77a1..a5fb22b7 100644
--- a/pkl-core/src/test/kotlin/org/pkl/core/project/ProjectDependenciesResolverTest.kt
+++ b/pkl-core/src/test/kotlin/org/pkl/core/project/ProjectDependenciesResolverTest.kt
@@ -6,6 +6,7 @@ import org.junit.jupiter.api.Test
 import org.junit.jupiter.api.assertThrows
 import org.pkl.commons.test.FileTestUtils
 import org.pkl.commons.test.PackageServer
+import org.pkl.commons.toPath
 import org.pkl.core.http.HttpClient
 import org.pkl.core.PklException
 import org.pkl.core.SecurityManagers
@@ -34,7 +35,7 @@ class ProjectDependenciesResolverTest {
 
   @Test
   fun resolveDependencies() {
-    val project2Path = Path.of(javaClass.getResource("project2/PklProject")!!.path)
+    val project2Path = javaClass.getResource("project2/PklProject")!!.toURI().toPath()
     val project = Project.loadFromPath(project2Path)
     val packageResolver = PackageResolver.getInstance(SecurityManagers.defaultManager, httpClient, null)
     val deps = ProjectDependenciesResolver(project, packageResolver, System.out.writer()).resolve()
@@ -72,7 +73,7 @@ class ProjectDependenciesResolverTest {
 
   @Test
   fun `fails if project declares a package with an incorrect checksum`() {
-    val projectPath = Path.of(javaClass.getResource("badProjectChecksum/PklProject")!!.path)
+    val projectPath = javaClass.getResource("badProjectChecksum/PklProject")!!.toURI().toPath()
     val project = Project.loadFromPath(projectPath)
     val packageResolver = PackageResolver.getInstance(SecurityManagers.defaultManager, httpClient, null)
     val e = assertThrows<PklException> {
diff --git a/pkl-core/src/test/kotlin/org/pkl/core/project/ProjectTest.kt b/pkl-core/src/test/kotlin/org/pkl/core/project/ProjectTest.kt
index 450dc088..4fc5cf7d 100644
--- a/pkl-core/src/test/kotlin/org/pkl/core/project/ProjectTest.kt
+++ b/pkl-core/src/test/kotlin/org/pkl/core/project/ProjectTest.kt
@@ -137,7 +137,7 @@ class ProjectTest {
   @Test
   fun `evaluate project module -- invalid checksum`() {
     PackageServer().use { server ->
-      val projectDir = Path.of(javaClass.getResource("badProjectChecksum2/")!!.path)
+      val projectDir = Path.of(javaClass.getResource("badProjectChecksum2/")!!.toURI())
       val project = Project.loadFromPath(projectDir.resolve("PklProject"))
       val httpClient = HttpClient.builder()
         .addCertificates(FileTestUtils.selfSignedCertificate)
diff --git a/pkl-core/src/test/kotlin/org/pkl/core/util/IoUtilsTest.kt b/pkl-core/src/test/kotlin/org/pkl/core/util/IoUtilsTest.kt
index 1e169df8..8f7034fb 100644
--- a/pkl-core/src/test/kotlin/org/pkl/core/util/IoUtilsTest.kt
+++ b/pkl-core/src/test/kotlin/org/pkl/core/util/IoUtilsTest.kt
@@ -117,70 +117,69 @@ class IoUtilsTest {
 
   @Test
   fun `relativize file URLs`() {
-    // perhaps URI("") would be a more precise result
     assertThat(
       IoUtils.relativize(
-        URI("file://foo/bar/baz.pkl"),
-        URI("file://foo/bar/baz.pkl")
+        URI("file:///foo/bar/baz.pkl"),
+        URI("file:///foo/bar/baz.pkl")
       )
     ).isEqualTo(URI("baz.pkl"))
 
     assertThat(
       IoUtils.relativize(
-        URI("file://foo/bar/baz.pkl"),
-        URI("file://foo/bar/qux.pkl")
+        URI("file:///foo/bar/baz.pkl"),
+        URI("file:///foo/bar/qux.pkl")
       )
     ).isEqualTo(URI("baz.pkl"))
 
     assertThat(
       IoUtils.relativize(
-        URI("file://foo/bar/baz.pkl"),
-        URI("file://foo/bar/")
+        URI("file:///foo/bar/baz.pkl"),
+        URI("file:///foo/bar/")
       )
     ).isEqualTo(URI("baz.pkl"))
 
     assertThat(
       IoUtils.relativize(
-        URI("file://foo/bar/baz.pkl"),
-        URI("file://foo/bar")
+        URI("file:///foo/bar/baz.pkl"),
+        URI("file:///foo/bar")
       )
     ).isEqualTo(URI("bar/baz.pkl"))
 
     // URI.relativize() returns an absolute URI here
     assertThat(
       IoUtils.relativize(
-        URI("file://foo/bar/baz.pkl"),
-        URI("file://foo/qux/")
+        URI("file:///foo/bar/baz.pkl"),
+        URI("file:///foo/qux/")
       )
     ).isEqualTo(URI("../bar/baz.pkl"))
 
     assertThat(
       IoUtils.relativize(
-        URI("file://foo/bar/baz.pkl"),
-        URI("file://foo/qux/qux2/")
+        URI("file:///foo/bar/baz.pkl"),
+        URI("file:///foo/qux/qux2/")
       )
     ).isEqualTo(URI("../../bar/baz.pkl"))
 
     assertThat(
       IoUtils.relativize(
-        URI("file://foo/bar/baz.pkl"),
-        URI("file://foo/qux/qux2")
+        URI("file:///foo/bar/baz.pkl"),
+        URI("file:///foo/qux/qux2")
       )
     ).isEqualTo(URI("../bar/baz.pkl"))
 
     assertThat(
       IoUtils.relativize(
-        URI("file://foo/bar/baz.pkl"),
-        URI("file://qux/qux2/")
+        URI("file:///foo/bar/baz.pkl"),
+        URI("file:///qux/qux2/")
       )
-    ).isEqualTo(URI("file://foo/bar/baz.pkl"))
+    ).isEqualTo(URI("../../foo/bar/baz.pkl"))
 
     assertThat(
       IoUtils.relativize(
-        URI("file://foo/bar/baz.pkl"),
-        URI("https://foo/bar/baz.pkl")
+        URI("file:///foo/bar/baz.pkl"),
+        URI("https:///foo/bar/baz.pkl")
       )
-    ).isEqualTo(URI("file://foo/bar/baz.pkl"))
+    ).isEqualTo(URI("file:///foo/bar/baz.pkl"))
   }
 
   @Test
@@ -343,7 +342,7 @@ class IoUtilsTest {
     val file3 = tempDir.resolve("base1/dir2/foo.pkl").createParentDirectories().createFile()
 
     val uri = file2.toUri()
-    val key = ModuleKeys.file(uri, file2)
+    val key = ModuleKeys.file(uri)
 
     assertThat(IoUtils.resolve(FakeSecurityManager, key, URI("..."))).isEqualTo(file1.toUri())
     assertThat(IoUtils.resolve(FakeSecurityManager, key, URI(".../foo.pkl"))).isEqualTo(file1.toUri())
diff --git a/pkl-core/src/test/resources/META-INF/services/org.junit.platform.engine.TestEngine b/pkl-core/src/test/resources/META-INF/services/org.junit.platform.engine.TestEngine
index 57e49043..9912afb4 100644
--- a/pkl-core/src/test/resources/META-INF/services/org.junit.platform.engine.TestEngine
+++ b/pkl-core/src/test/resources/META-INF/services/org.junit.platform.engine.TestEngine
@@ -4,3 +4,4 @@ org.pkl.core.MacAarch64LanguageSnippetTestsEngine
 org.pkl.core.LinuxAmd64LanguageSnippetTestsEngine
 org.pkl.core.LinuxAarch64LanguageSnippetTestsEngine
 org.pkl.core.AlpineLanguageSnippetTestsEngine
+org.pkl.core.WindowsLanguageSnippetTestsEngine
diff --git a/pkl-doc/src/main/kotlin/org/pkl/doc/CliDocGenerator.kt b/pkl-doc/src/main/kotlin/org/pkl/doc/CliDocGenerator.kt
index 13b34ef0..e9421521 100644
--- a/pkl-doc/src/main/kotlin/org/pkl/doc/CliDocGenerator.kt
+++ b/pkl-doc/src/main/kotlin/org/pkl/doc/CliDocGenerator.kt
@@ -22,6 +22,7 @@ import kotlin.Pair
 import org.pkl.commons.cli.CliBaseOptions.Companion.getProjectFile
 import org.pkl.commons.cli.CliCommand
 import org.pkl.commons.cli.CliException
+import org.pkl.commons.toPath
 import org.pkl.core.*
 import org.pkl.core.module.ModuleKeyFactories
 import org.pkl.core.packages.*
@@ -136,7 +137,7 @@ class CliDocGenerator(private val options: CliDocGeneratorOptions) : CliCommand(
     val packageUris = mutableListOf<PackageUri>()
     for (moduleUri in options.base.normalizedSourceModules) {
       if (moduleUri.scheme == "file") {
-        val dir = Path.of(moduleUri).parent
+        val dir = moduleUri.toPath().parent
         val projectFile = dir.getProjectFile(options.base.normalizedRootDir)
         if (projectFile != null) {
           pklProjectPaths.add(projectFile)
@@ -229,13 +230,12 @@ class CliDocGenerator(private val options: CliDocGeneratorOptions) : CliCommand(
             DocPackageInfo.fromPkl(module).apply {
               evaluator.collectImportedModules(overviewImports)
             }
-          schemasByDocPackageInfoAndPath[docPackageInfo to Path.of(uri.path).parent] =
-            mutableSetOf()
+          schemasByDocPackageInfoAndPath[docPackageInfo to uri.toPath().parent] = mutableSetOf()
         }
 
         for (uri in regularModuleUris) {
           val entry =
-            schemasByDocPackageInfoAndPath.keys.find { uri.path.startsWith(it.second.toString()) }
+            schemasByDocPackageInfoAndPath.keys.find { uri.toPath().startsWith(it.second) }
               ?: throw CliException("Could not find a doc-package-info.pkl for module $uri")
           val schema =
             evaluator.evaluateSchema(ModuleSource.uri(uri)).apply {
diff --git a/pkl-doc/src/main/kotlin/org/pkl/doc/DocGenerator.kt b/pkl-doc/src/main/kotlin/org/pkl/doc/DocGenerator.kt
index 05bd25a7..436f66ad 100644
--- a/pkl-doc/src/main/kotlin/org/pkl/doc/DocGenerator.kt
+++ b/pkl-doc/src/main/kotlin/org/pkl/doc/DocGenerator.kt
@@ -26,6 +26,7 @@ import org.pkl.commons.deleteRecursively
 import org.pkl.core.ModuleSchema
 import org.pkl.core.PClassInfo
 import org.pkl.core.Version
+import org.pkl.core.util.IoUtils
 
 /**
  * Entry point for the low-level Pkldoc API.
@@ -126,7 +127,7 @@ class DocGenerator(
       val dest = basePath.resolve("current")
       if (dest.exists() && dest.isSameFileAs(src)) continue
       dest.deleteIfExists()
-      dest.createSymbolicLinkPointingTo(basePath.relativize(src))
+      dest.createSymbolicLinkPointingTo(IoUtils.relativize(src, basePath))
     }
   }
 }
diff --git a/pkl-doc/src/main/kotlin/org/pkl/doc/Main.kt b/pkl-doc/src/main/kotlin/org/pkl/doc/Main.kt
index 8575d29c..1bc69150 100644
--- a/pkl-doc/src/main/kotlin/org/pkl/doc/Main.kt
+++ b/pkl-doc/src/main/kotlin/org/pkl/doc/Main.kt
@@ -28,6 +28,7 @@ import java.net.URI
 import java.nio.file.Path
 import org.pkl.commons.cli.cliMain
 import org.pkl.commons.cli.commands.BaseCommand
+import org.pkl.commons.cli.commands.BaseOptions.Companion.parseModuleName
 import org.pkl.commons.cli.commands.ProjectOptions
 import org.pkl.core.Release
 
diff --git a/pkl-doc/src/test/kotlin/org/pkl/doc/CliDocGeneratorTest.kt b/pkl-doc/src/test/kotlin/org/pkl/doc/CliDocGeneratorTest.kt
index 898cf445..290d7a0c 100644
--- a/pkl-doc/src/test/kotlin/org/pkl/doc/CliDocGeneratorTest.kt
+++ b/pkl-doc/src/test/kotlin/org/pkl/doc/CliDocGeneratorTest.kt
@@ -37,6 +37,7 @@ import org.pkl.commons.test.PackageServer
 import org.pkl.commons.test.listFilesRecursively
 import org.pkl.commons.toPath
 import org.pkl.core.Version
+import org.pkl.core.util.IoUtils
 import org.pkl.doc.DocGenerator.Companion.current
 
 class CliDocGeneratorTest {
@@ -92,11 +93,17 @@ class CliDocGeneratorTest {
     private val actualOutputFiles: List<Path> by lazy { actualOutputDir.listFilesRecursively() }
 
     private val expectedRelativeOutputFiles: List<String> by lazy {
-      expectedOutputFiles.map { expectedOutputDir.relativize(it).toString() }
+      expectedOutputFiles.map { path ->
+        IoUtils.toNormalizedPathString(expectedOutputDir.relativize(path)).let { str ->
+          // Git will by default clone symlinks as shortcuts on Windows, and shortcuts have a
+          // `.lnk` extension.
+          if (IoUtils.isWindows() && str.endsWith(".lnk")) str.dropLast(4) else str
+        }
+      }
     }
 
     private val actualRelativeOutputFiles: List<String> by lazy {
-      actualOutputFiles.map { actualOutputDir.relativize(it).toString() }
+      actualOutputFiles.map { IoUtils.toNormalizedPathString(actualOutputDir.relativize(it)) }
     }
 
     private val binaryFileExtensions =
@@ -219,6 +226,11 @@ class CliDocGeneratorTest {
       .withFailMessage("Test bug: $actualFile should exist but does not.")
       .exists()
 
+    // symlinks on Git and Windows is rather finnicky; they create shortcuts by default unless
+    // a core Git option is set. Also, by default, symlinks require administrator privileges to run.
+    // We'll just test that the symlink got created but skip verifying that it points to the right
+    // place.
+    if (actualFile.isSymbolicLink() && IoUtils.isWindows()) return
     val expectedFile = expectedOutputDir.resolve(relativeFilePath)
     if (expectedFile.exists()) {
       when {
diff --git a/pkl-doc/src/test/kotlin/org/pkl/doc/DocScopeTest.kt b/pkl-doc/src/test/kotlin/org/pkl/doc/DocScopeTest.kt
index 8b028f03..6a26a564 100644
--- a/pkl-doc/src/test/kotlin/org/pkl/doc/DocScopeTest.kt
+++ b/pkl-doc/src/test/kotlin/org/pkl/doc/DocScopeTest.kt
@@ -16,6 +16,7 @@
 package org.pkl.doc
 
 import java.net.URI
+import java.nio.file.Path
 import org.assertj.core.api.Assertions.assertThat
 import org.junit.jupiter.api.AfterAll
 import org.junit.jupiter.api.Test
@@ -221,6 +222,6 @@ class DocScopeTest {
     val scope = SiteScope(listOf(), mapOf(), { evaluator.evaluateSchema(uri(it)) }, outputDir)
 
     // used to return `/non/index.html`
-    assertThat(scope.url.path).isEqualTo("/non/existing/index.html")
+    assertThat(scope.url.toPath()).isEqualTo(Path.of("/non/existing/index.html").toAbsolutePath())
   }
 }
diff --git a/pkl-executor/pkl-executor.gradle.kts b/pkl-executor/pkl-executor.gradle.kts
index abd5b507..a93d7958 100644
--- a/pkl-executor/pkl-executor.gradle.kts
+++ b/pkl-executor/pkl-executor.gradle.kts
@@ -1,4 +1,5 @@
 import java.nio.file.Files
+import java.nio.file.LinkOption
 
 plugins {
   pklAllProjects
@@ -62,12 +63,23 @@ val prepareHistoricalDistributions by tasks.registering {
     val distributionDir = outputDir.get().asFile.toPath()
       .also(Files::createDirectories)
     for (file in pklHistoricalDistributions.files) {
-      val link = distributionDir.resolve(file.name)
-      if (!Files.isSymbolicLink(link)) {
-        if (Files.exists(link)) {
-          Files.delete(link)
+      val target = distributionDir.resolve(file.name)
+      // Create normal files on Windows, symlink on macOS/linux (need admin priveleges to create
+      // symlinks on Windows)
+      if (buildInfo.os.isWindows) {
+        if (!Files.isRegularFile(target, LinkOption.NOFOLLOW_LINKS)) {
+          if (Files.exists(target)) {
+            Files.delete(target)
+          }
+          Files.copy(file.toPath(), target)
+        }
+      } else {
+        if (!Files.isSymbolicLink(target)) {
+          if (Files.exists(target)) {
+            Files.delete(target)
+          }
+          Files.createSymbolicLink(target, file.toPath())
         }
-        Files.createSymbolicLink(link, file.toPath())
       }
     }
   }
diff --git a/pkl-executor/src/main/java/org/pkl/executor/EmbeddedExecutor.java b/pkl-executor/src/main/java/org/pkl/executor/EmbeddedExecutor.java
index 5dfbb963..3f1a4318 100644
--- a/pkl-executor/src/main/java/org/pkl/executor/EmbeddedExecutor.java
+++ b/pkl-executor/src/main/java/org/pkl/executor/EmbeddedExecutor.java
@@ -157,7 +157,15 @@ final class EmbeddedExecutor implements Executor {
 
   private static Path toDisplayPath(Path modulePath, ExecutorOptions options) {
     var rootDir = options.getRootDir();
-    return rootDir == null ? modulePath : rootDir.relativize(modulePath);
+    return rootDir == null ? modulePath : relativize(modulePath, rootDir);
+  }
+
+  // On Windows, `Path.relativize` will fail if the two paths have different roots.
+  private static Path relativize(Path path, Path base) {
+    if (path.isAbsolute() && base.isAbsolute() && !path.getRoot().equals(base.getRoot())) {
+      return path;
+    }
+    return base.relativize(path);
   }
 
   @Override
diff --git a/pkl-executor/src/test/kotlin/org/pkl/executor/EmbeddedExecutorTest.kt b/pkl-executor/src/test/kotlin/org/pkl/executor/EmbeddedExecutorTest.kt
index 97b85d0d..7a8d44c2 100644
--- a/pkl-executor/src/test/kotlin/org/pkl/executor/EmbeddedExecutorTest.kt
+++ b/pkl-executor/src/test/kotlin/org/pkl/executor/EmbeddedExecutorTest.kt
@@ -15,6 +15,7 @@ import org.pkl.commons.test.FilteringClassLoader
 import org.pkl.commons.test.PackageServer
 import org.pkl.commons.toPath
 import org.pkl.core.Release
+import java.io.File
 import java.nio.file.Files
 import java.nio.file.Path
 import java.time.Duration
@@ -197,9 +198,10 @@ class EmbeddedExecutorTest {
         Executors.embedded(listOf("/non/existing".toPath()))
     }
 
+    val sep = File.separatorChar
     assertThat(e.message)
       .contains("Cannot find Jar file")
-      .contains("/non/existing")
+      .contains("${sep}non${sep}existing")
   }
 
   @Test
diff --git a/pkl-gradle/src/main/java/org/pkl/gradle/task/ModulesTask.java b/pkl-gradle/src/main/java/org/pkl/gradle/task/ModulesTask.java
index 3acc52e8..8717a280 100644
--- a/pkl-gradle/src/main/java/org/pkl/gradle/task/ModulesTask.java
+++ b/pkl-gradle/src/main/java/org/pkl/gradle/task/ModulesTask.java
@@ -134,7 +134,7 @@ public abstract class ModulesTask extends BasePklTask {
    */
   private URI parsedModuleNotationToUri(Object notation) {
     if (notation instanceof File file) {
-      return IoUtils.createUri(file.getPath());
+      return IoUtils.createUri(IoUtils.toNormalizedPathString(file.toPath()));
     } else if (notation instanceof URI uri) {
       return uri;
     }
diff --git a/pkl-gradle/src/test/kotlin/org/pkl/gradle/EvaluatorsTest.kt b/pkl-gradle/src/test/kotlin/org/pkl/gradle/EvaluatorsTest.kt
index 56326abd..ccd58ca4 100644
--- a/pkl-gradle/src/test/kotlin/org/pkl/gradle/EvaluatorsTest.kt
+++ b/pkl-gradle/src/test/kotlin/org/pkl/gradle/EvaluatorsTest.kt
@@ -2,7 +2,9 @@ package org.pkl.gradle
 
 import org.assertj.core.api.Assertions
 import org.pkl.commons.readString
+import org.pkl.commons.readString
 import org.pkl.commons.test.PackageServer
+import org.pkl.commons.toNormalizedPathString
 import org.assertj.core.api.Assertions.assertThat
 import org.junit.jupiter.api.Test
 import org.junit.jupiter.api.io.TempDir
@@ -199,8 +201,8 @@ class EvaluatorsTest : AbstractTest() {
 
   @Test
   fun `source module URIs`() {
-    val pklFile = writeFile(
-      "test.pkl", """
+    writeFile(
+      "testDir/test.pkl", """
       person {
         name = "Pigeon"
         age = 20 + 10
@@ -218,7 +220,7 @@ class EvaluatorsTest : AbstractTest() {
         evaluators {
           evalTest {
             sourceModules = [uri("modulepath:/test.pkl")]
-            modulePath.from "${pklFile.parent}"
+            modulePath.from layout.projectDirectory.dir("testDir")
             outputFile = layout.projectDirectory.file("test.pcf")
             settingsModule = "pkl:settings"
           }
@@ -387,7 +389,7 @@ class EvaluatorsTest : AbstractTest() {
   @Test
   fun `explicitly set cache dir`(@TempDir tempDir: Path) {
     writeBuildFile("pcf", """
-      moduleCacheDir = file("$tempDir")
+      moduleCacheDir = file("${tempDir.toUri()}")
     """.trimIndent())
     writeFile(
       "test.pkl",
diff --git a/pkl-gradle/src/test/kotlin/org/pkl/gradle/TestsTest.kt b/pkl-gradle/src/test/kotlin/org/pkl/gradle/TestsTest.kt
index 46dc235b..769ec540 100644
--- a/pkl-gradle/src/test/kotlin/org/pkl/gradle/TestsTest.kt
+++ b/pkl-gradle/src/test/kotlin/org/pkl/gradle/TestsTest.kt
@@ -1,6 +1,7 @@
 package org.pkl.gradle
 
 import org.assertj.core.api.Assertions.assertThat
+import org.pkl.commons.toNormalizedPathString
 import org.junit.jupiter.api.Test
 import java.nio.file.Path
 import kotlin.io.path.readText
@@ -46,8 +47,7 @@ class TestsTest : AbstractTest() {
 
     val output = runTask("evalTest", expectFailure = true).output.stripFilesAndLines()
 
-    assertThat(output.trimStart()).startsWith("""
-      > Task :evalTest FAILED
+    assertThat(output).contains("""
       module test (file:///file, line x)
         test ❌
           Error:
@@ -143,7 +143,7 @@ class TestsTest : AbstractTest() {
     val pklFile = writePklFile(contents = bigTest)
     writeFile("test.pkl-expected.pcf", bigTestExpected)
 
-    writeBuildFile("junitReportsDir = file('${pklFile.parent}/build')")
+    writeBuildFile("junitReportsDir = file('${pklFile.parent.toNormalizedPathString()}/build')")
 
     runTask("evalTest", expectFailure = true)
 
diff --git a/pkl-server/src/test/kotlin/org/pkl/server/BinaryEvaluatorSnippetTests.kt b/pkl-server/src/test/kotlin/org/pkl/server/BinaryEvaluatorSnippetTests.kt
index ba303dab..b530d888 100644
--- a/pkl-server/src/test/kotlin/org/pkl/server/BinaryEvaluatorSnippetTests.kt
+++ b/pkl-server/src/test/kotlin/org/pkl/server/BinaryEvaluatorSnippetTests.kt
@@ -58,7 +58,8 @@ class BinaryEvaluatorSnippetTestEngine : InputOutputTestEngine() {
       null
     )
 
-  private fun String.stripFilePaths() = replace(snippetsDir.toString(), "/\$snippetsDir")
+  private fun String.stripFilePaths() =
+    replace(snippetsDir.toUri().toString(), "file:///\$snippetsDir/")
 
   override fun generateOutputFor(inputFile: Path): Pair<Boolean, String> {
     val bytes = evaluator.evaluate(ModuleSource.path(inputFile), null)
diff --git a/stdlib/platform.pkl b/stdlib/platform.pkl
index 088e8bbc..c7d5297e 100644
--- a/stdlib/platform.pkl
+++ b/stdlib/platform.pkl
@@ -66,7 +66,7 @@ class VirtualMachine {
 /// The operating system of a platform.
 class OperatingSystem {
   /// The name of this operating system.
-  name: String
+  name: "macOS"|"Linux"|"Windows"|String
 
   /// The version of this operating system.
   version: String