diff --git a/src/main/agent-detector.ts b/src/main/agent-detector.ts
index 67a10a4f..c666bc95 100644
--- a/src/main/agent-detector.ts
+++ b/src/main/agent-detector.ts
@@ -325,6 +325,8 @@ export class AgentDetector {
         path.join(localAppData, 'npm'),
         // Claude Code CLI install location (npm global)
         path.join(appData, 'npm', 'node_modules', '@anthropic-ai', 'claude-code', 'cli'),
+        // User local bin (Claude Code standalone installer)
+        path.join(home, '.local', 'bin'),
         // User local programs
         path.join(localAppData, 'Programs'),
         path.join(localAppData, 'Microsoft', 'WindowsApps'),
@@ -384,6 +386,7 @@ export class AgentDetector {
 
   /**
    * Check if a binary exists in PATH
+   * On Windows, this also handles .cmd and .exe extensions properly
    */
   private async checkBinaryExists(binaryName: string): Promise<{ exists: boolean; path?: string }> {
     try {
@@ -396,9 +399,56 @@ export class AgentDetector {
       const result = await execFileNoThrow(command, [binaryName], undefined, env);
 
       if (result.exitCode === 0 && result.stdout.trim()) {
+        // Get all matches (Windows 'where' can return multiple)
+        const matches = result.stdout.trim().split('\n').map(p => p.trim()).filter(p => p);
+
+        if (process.platform === 'win32' && matches.length > 0) {
+          // On Windows, prefer .exe over .cmd over extensionless
+          // This helps with proper execution handling
+          const exeMatch = matches.find(p => p.toLowerCase().endsWith('.exe'));
+          const cmdMatch = matches.find(p => p.toLowerCase().endsWith('.cmd'));
+
+          // Return the best match: .exe > .cmd > first result
+          let bestMatch = exeMatch || cmdMatch || matches[0];
+
+          // If the first match doesn't have an extension, check if .cmd or .exe version exists
+          // This handles cases where 'where' returns a path without extension
+          if (!bestMatch.toLowerCase().endsWith('.exe') && !bestMatch.toLowerCase().endsWith('.cmd')) {
+            const cmdPath = bestMatch + '.cmd';
+            const exePath = bestMatch + '.exe';
+
+            // Check if the .exe or .cmd version exists
+            try {
+              await fs.promises.access(exePath, fs.constants.F_OK);
+              bestMatch = exePath;
+              logger.debug(`Found .exe version of ${binaryName}`, 'AgentDetector', { path: exePath });
+            } catch {
+              try {
+                await fs.promises.access(cmdPath, fs.constants.F_OK);
+                bestMatch = cmdPath;
+                logger.debug(`Found .cmd version of ${binaryName}`, 'AgentDetector', { path: cmdPath });
+              } catch {
+                // Neither .exe nor .cmd exists, use the original path
+              }
+            }
+          }
+
+          logger.debug(`Windows binary detection for ${binaryName}`, 'AgentDetector', {
+            allMatches: matches,
+            selectedMatch: bestMatch,
+            isCmd: bestMatch.toLowerCase().endsWith('.cmd'),
+            isExe: bestMatch.toLowerCase().endsWith('.exe'),
+          });
+
+          return {
+            exists: true,
+            path: bestMatch,
+          };
+        }
+
         return {
           exists: true,
-          path: result.stdout.trim().split('\n')[0], // First match
+          path: matches[0], // First match for Unix
         };
       }
 
diff --git a/src/main/process-manager.ts b/src/main/process-manager.ts
index dd407061..fa8eeda2 100644
--- a/src/main/process-manager.ts
+++ b/src/main/process-manager.ts
@@ -537,10 +537,26 @@ export class ProcessManager extends EventEmitter {
           hasStdio: 'default (pipe)'
         });
 
-        const childProcess = spawn(command, finalArgs, {
+        // On Windows, .cmd files (npm-installed CLIs) need special handling
+        // They must be executed through cmd.exe since spawn() with shell:false
+        // cannot execute batch scripts directly
+        let spawnCommand = command;
+        let spawnArgs = finalArgs;
+        let useShell = false;
+
+        if (isWindows && command.toLowerCase().endsWith('.cmd')) {
+          // For .cmd files, we need to use shell:true to execute them properly
+          // This is safe because we're executing a specific file path, not user input
+          useShell = true;
+          logger.debug('[ProcessManager] Using shell=true for Windows .cmd file', 'ProcessManager', {
+            command,
+          });
+        }
+
+        const childProcess = spawn(spawnCommand, spawnArgs, {
           cwd,
           env,
-          shell: false, // Explicitly disable shell to prevent injection
+          shell: useShell, // Enable shell only for .cmd files on Windows
           stdio: ['pipe', 'pipe', 'pipe'], // Explicitly set stdio to pipe
         });
 
diff --git a/src/main/utils/execFile.ts b/src/main/utils/execFile.ts
index bed1b818..6d2f7bab 100644
--- a/src/main/utils/execFile.ts
+++ b/src/main/utils/execFile.ts
@@ -15,6 +15,9 @@ export interface ExecResult {
 /**
  * Safely execute a command without shell injection vulnerabilities
  * Uses execFile instead of exec to prevent shell interpretation
+ *
+ * On Windows, .cmd files (npm-installed CLIs) are handled by enabling shell mode,
+ * since execFile cannot directly execute batch scripts without the shell.
  */
 export async function execFileNoThrow(
   command: string,
@@ -23,11 +26,17 @@ export async function execFileNoThrow(
   env?: NodeJS.ProcessEnv
 ): Promise<ExecResult> {
   try {
+    // On Windows, .cmd files need shell execution
+    // This is safe because we're executing a specific file path, not user input
+    const isWindows = process.platform === 'win32';
+    const needsShell = isWindows && command.toLowerCase().endsWith('.cmd');
+
     const { stdout, stderr } = await execFileAsync(command, args, {
       cwd,
       env,
       encoding: 'utf8',
       maxBuffer: EXEC_MAX_BUFFER,
+      shell: needsShell,
     });
 
     return {