diff --git a/Cargo.lock b/Cargo.lock
index 4783055f..c91ba607 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -874,6 +874,7 @@ dependencies = [
  "dunce",
  "fs-tail",
  "heck 0.5.0",
+ "komorebi-client",
  "komorebi-core",
  "lazy_static",
  "miette",
diff --git a/komorebi-client/src/lib.rs b/komorebi-client/src/lib.rs
index 621753db..27fb227a 100644
--- a/komorebi-client/src/lib.rs
+++ b/komorebi-client/src/lib.rs
@@ -16,6 +16,7 @@ pub use komorebi::NotificationEvent;
 pub use komorebi::RuleDebug;
 pub use komorebi::StackbarConfig;
 pub use komorebi::State;
+pub use komorebi::StaticConfig;
 pub use komorebi::TabsConfig;
 pub use komorebi_core::ActiveWindowBorderStyle;
 pub use komorebi_core::Arrangement;
diff --git a/komorebic/Cargo.toml b/komorebic/Cargo.toml
index 3296956b..7ae99ab9 100644
--- a/komorebic/Cargo.toml
+++ b/komorebic/Cargo.toml
@@ -13,6 +13,7 @@ edition = "2021"
 [dependencies]
 derive-ahk = { path = "../derive-ahk" }
 komorebi-core = { path = "../komorebi-core" }
+komorebi-client = { path = "../komorebi-client" }
 
 clap = { version = "4", features = ["derive", "wrap_help"] }
 color-eyre = { workspace = true }
diff --git a/komorebic/src/main.rs b/komorebic/src/main.rs
index 934b9c33..95abb834 100644
--- a/komorebic/src/main.rs
+++ b/komorebic/src/main.rs
@@ -1391,6 +1391,11 @@ fn main() -> Result<()> {
                     }
                 }
 
+                // Check that this file adheres to the schema static config schema as the last step,
+                // so that more basic errors above can be shown to the error before schema-specific
+                // errors
+                let _ = serde_json::from_str::<komorebi_client::StaticConfig>(&config_source)?;
+
                 if config_whkd.exists() {
                     println!("Found {}; key bindings will be loaded from here when whkd is started, and you can start it automatically using the --whkd flag\n", config_whkd.to_string_lossy());
                 } else {
@@ -1775,7 +1780,7 @@ fn main() -> Result<()> {
             };
 
             let mut flags = vec![];
-            if let Some(config) = arg.config {
+            if let Some(config) = &arg.config {
                 let path = resolve_home_path(config)?;
                 if !path.is_file() {
                     bail!("could not find file: {}", path.display());
@@ -1810,9 +1815,10 @@ fn main() -> Result<()> {
                 )
             };
 
+            let mut attempts = 0;
             let mut running = false;
 
-            while !running {
+            while !running && attempts <= 2 {
                 match powershell_script::run(&script) {
                     Ok(_) => {
                         println!("{script}");
@@ -1833,9 +1839,27 @@ fn main() -> Result<()> {
                     running = true;
                 } else {
                     println!("komorebi.exe did not start... Trying again");
+                    attempts += 1;
                 }
             }
 
+            if !running {
+                println!("\nRunning komorebi.exe directly for detailed error output\n");
+                if let Some(config) = arg.config {
+                    let path = resolve_home_path(config)?;
+                    if let Ok(output) = Command::new("komorebi.exe")
+                        .arg(format!("'--config=\"{}\"'", path.display()))
+                        .output()
+                    {
+                        println!("{}", String::from_utf8(output.stderr)?);
+                    }
+                } else if let Ok(output) = Command::new("komorebi.exe").output() {
+                    println!("{}", String::from_utf8(output.stderr)?);
+                }
+
+                return Ok(());
+            }
+
             if arg.whkd {
                 let script = r"
 if (!(Get-Process whkd -ErrorAction SilentlyContinue))