diff --git a/src/tools/image.ts b/src/tools/image.ts
index 8cb85b4..78d2ffe 100644
--- a/src/tools/image.ts
+++ b/src/tools/image.ts
@@ -56,7 +56,7 @@ export async function imageToolHandler(
 
     const args = buildSwiftCliArgs(input, effectivePath, swiftFormat, logger);
 
-    const swiftResponse = await executeSwiftCli(args, logger);
+    const swiftResponse = await executeSwiftCli(args, logger, { timeout: 30000 });
 
     if (!swiftResponse.success) {
       logger.error(
diff --git a/src/tools/list.ts b/src/tools/list.ts
index dfd2d41..18849a9 100644
--- a/src/tools/list.ts
+++ b/src/tools/list.ts
@@ -115,7 +115,7 @@ export async function listToolHandler(
     const args = buildSwiftCliArgs(input);
 
     // Execute Swift CLI
-    const swiftResponse = await executeSwiftCli(args, logger);
+    const swiftResponse = await executeSwiftCli(args, logger, { timeout: 15000 });
 
     if (!swiftResponse.success) {
       logger.error({ error: swiftResponse.error }, "Swift CLI returned error");
diff --git a/src/utils/peekaboo-cli.ts b/src/utils/peekaboo-cli.ts
index ae23bb1..39e43cd 100644
--- a/src/utils/peekaboo-cli.ts
+++ b/src/utils/peekaboo-cli.ts
@@ -102,6 +102,7 @@ function mapExitCodeToErrorMessage(
 export async function executeSwiftCli(
   args: string[],
   logger: Logger,
+  options: { timeout?: number } = {},
 ): Promise<SwiftCliResponse> {
   let cliPath: string;
   try {
@@ -121,13 +122,54 @@ export async function executeSwiftCli(
   // Always add --json-output flag
   const fullArgs = [...args, "--json-output"];
 
-  logger.debug({ command: cliPath, args: fullArgs }, "Executing Swift CLI");
+  // Default timeout of 30 seconds, configurable via options or environment variable
+  const defaultTimeout = parseInt(process.env.PEEKABOO_CLI_TIMEOUT || "30000", 10);
+  const timeoutMs = options.timeout || defaultTimeout;
+
+  logger.debug({ command: cliPath, args: fullArgs, timeoutMs }, "Executing Swift CLI");
 
   return new Promise((resolve) => {
     const process = spawn(cliPath, fullArgs);
 
     let stdout = "";
     let stderr = "";
+    let isResolved = false;
+
+    // Set up timeout
+    const timeoutId = setTimeout(() => {
+      if (!isResolved) {
+        isResolved = true;
+        logger.error(
+          { timeoutMs, command: cliPath, args: fullArgs },
+          "Swift CLI execution timed out"
+        );
+        
+        // Kill the process
+        process.kill('SIGTERM');
+        
+        // Give it a moment to terminate gracefully, then force kill
+        setTimeout(() => {
+          if (!process.killed) {
+            process.kill('SIGKILL');
+          }
+        }, 1000);
+
+        resolve({
+          success: false,
+          error: {
+            message: `Swift CLI execution timed out after ${timeoutMs}ms. This may indicate a permission dialog is waiting for user input, or the process is stuck.`,
+            code: "SWIFT_CLI_TIMEOUT",
+            details: `Command: ${cliPath} ${fullArgs.join(' ')}`,
+          },
+        });
+      }
+    }, timeoutMs);
+
+    const cleanup = () => {
+      if (timeoutId) {
+        clearTimeout(timeoutId);
+      }
+    };
 
     process.stdout.on("data", (data: Buffer | string) => {
       stdout += data.toString();
@@ -141,6 +183,13 @@ export async function executeSwiftCli(
     });
 
     process.on("close", (exitCode: number | null) => {
+      cleanup();
+      
+      if (isResolved) {
+        return; // Already resolved due to timeout
+      }
+      isResolved = true;
+
       logger.debug(
         { exitCode, stdout: stdout.slice(0, 200) },
         "Swift CLI completed",
@@ -261,6 +310,13 @@ export async function executeSwiftCli(
     });
 
     process.on("error", (error: Error) => {
+      cleanup();
+      
+      if (isResolved) {
+        return; // Already resolved due to timeout
+      }
+      isResolved = true;
+
       logger.error({ error }, "Failed to spawn Swift CLI process");
       resolve({
         success: false,
@@ -283,14 +339,44 @@ export async function readImageAsBase64(imagePath: string): Promise<string> {
 export async function execPeekaboo(
   args: string[],
   packageRootDir: string,
-  options: { expectSuccess?: boolean } = {},
+  options: { expectSuccess?: boolean; timeout?: number } = {},
 ): Promise<{ success: boolean; data?: string; error?: string }> {
   const cliPath = process.env.PEEKABOO_CLI_PATH || path.resolve(packageRootDir, "peekaboo");
+  const timeoutMs = options.timeout || 15000; // Default 15 seconds for simple commands
 
   return new Promise((resolve) => {
     const process = spawn(cliPath, args);
     let stdout = "";
     let stderr = "";
+    let isResolved = false;
+
+    // Set up timeout
+    const timeoutId = setTimeout(() => {
+      if (!isResolved) {
+        isResolved = true;
+        
+        // Kill the process
+        process.kill('SIGTERM');
+        
+        // Give it a moment to terminate gracefully, then force kill
+        setTimeout(() => {
+          if (!process.killed) {
+            process.kill('SIGKILL');
+          }
+        }, 1000);
+
+        resolve({ 
+          success: false, 
+          error: `Command timed out after ${timeoutMs}ms: ${cliPath} ${args.join(' ')}` 
+        });
+      }
+    }, timeoutMs);
+
+    const cleanup = () => {
+      if (timeoutId) {
+        clearTimeout(timeoutId);
+      }
+    };
 
     process.stdout.on("data", (data) => {
       stdout += data.toString();
@@ -301,6 +387,13 @@ export async function execPeekaboo(
     });
 
     process.on("close", (code) => {
+      cleanup();
+      
+      if (isResolved) {
+        return; // Already resolved due to timeout
+      }
+      isResolved = true;
+
       const success = code === 0;
       if (options.expectSuccess !== false && !success) {
         resolve({ success: false, error: stderr || stdout });
@@ -310,6 +403,13 @@ export async function execPeekaboo(
     });
 
     process.on("error", (err) => {
+      cleanup();
+      
+      if (isResolved) {
+        return; // Already resolved due to timeout
+      }
+      isResolved = true;
+
       resolve({ success: false, error: err.message });
     });
   });
diff --git a/vitest.config.ts b/vitest.config.ts
index 8b43659..2879cf9 100644
--- a/vitest.config.ts
+++ b/vitest.config.ts
@@ -7,9 +7,24 @@ export default defineConfig({
     include: [
       "**/tests/unit/**/*.test.ts",
       "**/tests/integration/**/*.test.ts",
-      "peekaboo-cli/tests/e2e/**/*.test.ts",
+      // Only include E2E tests if running on macOS and not in CI
+      ...(process.platform === "darwin" && !process.env.CI 
+        ? ["peekaboo-cli/tests/e2e/**/*.test.ts"] 
+        : []
+      ),
     ],
-    exclude: ["**/node_modules/**", "**/dist/**"],
+    exclude: [
+      "**/node_modules/**", 
+      "**/dist/**",
+      // Exclude E2E tests in CI or non-macOS environments
+      ...(process.platform !== "darwin" || process.env.CI 
+        ? ["peekaboo-cli/tests/e2e/**/*.test.ts"] 
+        : []
+      ),
+    ],
+    // Set reasonable timeouts to prevent hanging
+    testTimeout: 60000, // 60 seconds for individual tests
+    hookTimeout: 30000, // 30 seconds for setup/teardown hooks
     coverage: {
       provider: "v8",
       reporter: ["text", "lcov", "html"],