diff --git a/crates-cli/yaak-cli/src/main.rs b/crates-cli/yaak-cli/src/main.rs
index ba439c1f..b5a2ad30 100644
--- a/crates-cli/yaak-cli/src/main.rs
+++ b/crates-cli/yaak-cli/src/main.rs
@@ -10,6 +10,7 @@ mod version_check;
 use clap::Parser;
 use cli::{Cli, Commands, PluginCommands, RequestCommands};
 use context::{CliContext, CliExecutionContext};
+use std::path::PathBuf;
 use yaak_models::queries::any_request::AnyRequest;
 
 #[tokio::main]
@@ -30,9 +31,7 @@ async fn main() {
 
     let app_id = if cfg!(debug_assertions) { "app.yaak.desktop.dev" } else { "app.yaak.desktop" };
 
-    let data_dir = data_dir.unwrap_or_else(|| {
-        dirs::data_dir().expect("Could not determine data directory").join(app_id)
-    });
+    let data_dir = data_dir.unwrap_or_else(|| resolve_data_dir(app_id));
 
     version_check::maybe_check_for_updates().await;
 
@@ -239,3 +238,46 @@ fn resolve_cookie_jar_id(
         .map(|jar| jar.id);
     Ok(default_cookie_jar)
 }
+
+fn resolve_data_dir(app_id: &str) -> PathBuf {
+    if let Some(dir) = wsl_data_dir(app_id) {
+        return dir;
+    }
+    dirs::data_dir().expect("Could not determine data directory").join(app_id)
+}
+
+/// Detect WSL and resolve the Windows AppData\Roaming path for the Yaak data directory.
+fn wsl_data_dir(app_id: &str) -> Option<PathBuf> {
+    if !cfg!(target_os = "linux") {
+        return None;
+    }
+
+    let proc_version = std::fs::read_to_string("/proc/version").ok()?;
+    let is_wsl = proc_version.to_lowercase().contains("microsoft");
+    if !is_wsl {
+        return None;
+    }
+
+    // We're in WSL, so try to resolve the Yaak app's data directory in Windows
+
+    // Get the Windows %APPDATA% path via cmd.exe
+    let appdata_output =
+        std::process::Command::new("cmd.exe").args(["/C", "echo", "%APPDATA%"]).output().ok()?;
+
+    let win_path = String::from_utf8(appdata_output.stdout).ok()?.trim().to_string();
+    if win_path.is_empty() || win_path == "%APPDATA%" {
+        return None;
+    }
+
+    // Convert Windows path to WSL path using wslpath (handles custom mount points)
+    let wslpath_output = std::process::Command::new("wslpath").arg(&win_path).output().ok()?;
+
+    let wsl_appdata = String::from_utf8(wslpath_output.stdout).ok()?.trim().to_string();
+    if wsl_appdata.is_empty() {
+        return None;
+    }
+
+    let wsl_path = PathBuf::from(wsl_appdata).join(app_id);
+
+    if wsl_path.exists() { Some(wsl_path) } else { None }
+}