diff --git a/src/main/utils/metadataExtraction.ts b/src/main/utils/metadataExtraction.ts
index 8281d9bc..e43c80d0 100644
--- a/src/main/utils/metadataExtraction.ts
+++ b/src/main/utils/metadataExtraction.ts
@@ -13,6 +13,17 @@ import type { FileSystemProvider } from '../services/infrastructure/FileSystemPr
 
 const logger = createLogger('Util:metadataExtraction');
 
+/**
+ * Normalize Windows drive letter to uppercase for consistent path comparison.
+ * CLI uses uppercase (C:\...) while VS Code extension uses lowercase (c:\...).
+ */
+function normalizeDriveLetter(p: string): string {
+  if (p.length >= 2 && p[1] === ':') {
+    return p[0].toUpperCase() + p.slice(1);
+  }
+  return p;
+}
+
 const defaultProvider = new LocalFileSystemProvider();
 
 interface MessagePreview {
@@ -48,7 +59,7 @@ export async function extractCwd(
       if ('cwd' in entry && entry.cwd) {
         rl.close();
         fileStream.destroy();
-        return entry.cwd;
+        return normalizeDriveLetter(entry.cwd);
       }
     }
   } catch (error) {
diff --git a/test/main/services/discovery/SessionSearcher.test.ts b/test/main/services/discovery/SessionSearcher.test.ts
index 88aa36b7..385fa83c 100644
--- a/test/main/services/discovery/SessionSearcher.test.ts
+++ b/test/main/services/discovery/SessionSearcher.test.ts
@@ -10,7 +10,7 @@ describe('SessionSearcher', () => {
 
   afterEach(() => {
     for (const dir of tempDirs) {
-      fs.rmSync(dir, { recursive: true, force: true });
+      fs.rmSync(dir, { recursive: true, force: true, maxRetries: 3, retryDelay: 100 });
     }
     tempDirs.length = 0;
   });