diff --git a/README.md b/README.md
index f43cc2b..86fb6a4 100644
--- a/README.md
+++ b/README.md
@@ -80,6 +80,7 @@ Peekaboo can be configured using environment variables:
 
 ```json
 {
+  "PEEKABOO_AI_PROVIDERS": "ollama/llava:latest,openai/gpt-4o",
   "PEEKABOO_LOG_LEVEL": "debug",
   "PEEKABOO_LOG_FILE": "~/Library/Logs/peekaboo-mcp-debug.log",
   "PEEKABOO_DEFAULT_SAVE_PATH": "~/Pictures/PeekabooCaptures",
diff --git a/src/utils/peekaboo-cli.ts b/src/utils/peekaboo-cli.ts
index a9393da..27cc1eb 100644
--- a/src/utils/peekaboo-cli.ts
+++ b/src/utils/peekaboo-cli.ts
@@ -142,14 +142,10 @@ export async function executeSwiftCli(
         
         // Kill the process with SIGTERM first
         try {
-          try {
           process.kill('SIGTERM');
         } catch (err) {
           // Process might already be dead
         }
-        } catch (err) {
-          // Process might already be dead
-        }
         
         // Give it a moment to terminate gracefully, then force kill
         setTimeout(() => {
@@ -165,7 +161,11 @@ export async function executeSwiftCli(
 
         resolve({ 
           success: false, 
-          error: `Command timed out after ${timeoutMs}ms: ${cliPath} ${args.join(' ')}` 
+          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);
diff --git a/tests/integration/image-tool.test.ts b/tests/integration/image-tool.test.ts
index 6032c0d..25df92e 100644
--- a/tests/integration/image-tool.test.ts
+++ b/tests/integration/image-tool.test.ts
@@ -109,7 +109,8 @@ describeSwiftTests("Image Tool Integration Tests", () => {
       // The CLI should be called with the DIRECTORY, not a full file path
       expect(mockExecuteSwiftCli).toHaveBeenCalledWith(
         expect.arrayContaining(["--path", MOCK_TEMP_DIR]),
-        mockContext.logger
+        mockContext.logger,
+        expect.objectContaining({ timeout: expect.any(Number) })
       );
 
       // Verify the result is correct
@@ -149,7 +150,8 @@ describeSwiftTests("Image Tool Integration Tests", () => {
       expect(mockResolveImagePath).toHaveBeenCalledWith({}, mockContext.logger);
       expect(mockExecuteSwiftCli).toHaveBeenCalledWith(
         expect.arrayContaining(["--path", MOCK_TEMP_DIR]),
-        mockContext.logger
+        mockContext.logger,
+        expect.objectContaining({ timeout: expect.any(Number) })
       );
     });
   });
@@ -201,7 +203,8 @@ describeSwiftTests("Image Tool Integration Tests", () => {
       expect(result.isError).toBeFalsy();
       expect(mockExecuteSwiftCli).toHaveBeenCalledWith(
         expect.arrayContaining(["image", "--mode", "screen", "--screen-index", "0"]),
-        mockContext.logger
+        mockContext.logger,
+        expect.objectContaining({ timeout: expect.any(Number) })
       );
       // Since temp dir was used, saved_files now contains the temp file
       const mockResponse = mockSwiftCli.captureImage("screen", {
@@ -239,7 +242,8 @@ describeSwiftTests("Image Tool Integration Tests", () => {
       );
       expect(mockExecuteSwiftCli).toHaveBeenCalledWith(
         expect.not.arrayContaining(["--screen-index"]),
-        mockContext.logger
+        mockContext.logger,
+        expect.objectContaining({ timeout: expect.any(Number) })
       );
     });
 
@@ -272,7 +276,8 @@ describeSwiftTests("Image Tool Integration Tests", () => {
       expect(result.isError).toBeFalsy();
       expect(mockExecuteSwiftCli).toHaveBeenCalledWith(
         expect.arrayContaining(["image", "--mode", "screen", "--screen-index", "99"]),
-        mockContext.logger
+        mockContext.logger,
+        expect.objectContaining({ timeout: expect.any(Number) })
       );
       // Since temp dir was used, saved_files now contains the temp file
       expect(result.saved_files).toEqual([{
@@ -900,7 +905,8 @@ describeSwiftTests("Image Tool Integration Tests", () => {
       // It should have used the default path
       expect(mockExecuteSwiftCli).toHaveBeenCalledWith(
         expect.arrayContaining(["--path", MOCK_DEFAULT_PATH]),
-        mockContext.logger
+        mockContext.logger,
+        expect.objectContaining({ timeout: expect.any(Number) })
       );
       
       // No cleanup should have occurred
@@ -942,7 +948,8 @@ describeSwiftTests("Image Tool Integration Tests", () => {
       // We can verify this by checking that the Swift CLI was called with the temp dir, not the default path
       expect(mockExecuteSwiftCli).toHaveBeenCalledWith(
         expect.arrayContaining(["--path", MOCK_TEMP_DIR]),
-        mockContext.logger
+        mockContext.logger,
+        expect.objectContaining({ timeout: expect.any(Number) })
       );
 
       delete process.env.PEEKABOO_DEFAULT_SAVE_PATH;
diff --git a/tests/unit/tools/image-edge-cases.test.ts b/tests/unit/tools/image-edge-cases.test.ts
index edbef2d..eaf1395 100644
--- a/tests/unit/tools/image-edge-cases.test.ts
+++ b/tests/unit/tools/image-edge-cases.test.ts
@@ -103,6 +103,7 @@ describe("Image Tool - Edge Cases", () => {
           "--window-title", "Apple"
         ]),
         mockLogger,
+        expect.objectContaining({ timeout: expect.any(Number) })
       );
     });
   });
@@ -128,6 +129,7 @@ describe("Image Tool - Edge Cases", () => {
       expect(mockExecuteSwiftCli).toHaveBeenCalledWith(
         expect.arrayContaining(["--format", "png"]),
         mockLogger,
+        expect.objectContaining({ timeout: expect.any(Number) })
       );
     });
 
@@ -151,6 +153,7 @@ describe("Image Tool - Edge Cases", () => {
       expect(mockExecuteSwiftCli).toHaveBeenCalledWith(
         expect.arrayContaining(["--format", "jpg"]),
         mockLogger,
+        expect.objectContaining({ timeout: expect.any(Number) })
       );
     });
 
@@ -174,6 +177,7 @@ describe("Image Tool - Edge Cases", () => {
       expect(mockExecuteSwiftCli).toHaveBeenCalledWith(
         expect.arrayContaining(["--format", "jpg"]),
         mockLogger,
+        expect.objectContaining({ timeout: expect.any(Number) })
       );
     });
 
@@ -197,6 +201,7 @@ describe("Image Tool - Edge Cases", () => {
       expect(mockExecuteSwiftCli).toHaveBeenCalledWith(
         expect.arrayContaining(["--format", "jpg"]),
         mockLogger,
+        expect.objectContaining({ timeout: expect.any(Number) })
       );
     });
 
@@ -222,6 +227,7 @@ describe("Image Tool - Edge Cases", () => {
       expect(mockExecuteSwiftCli).toHaveBeenCalledWith(
         expect.arrayContaining(["--format", "png"]),
         mockLogger,
+        expect.objectContaining({ timeout: expect.any(Number) })
       );
     });
   });
@@ -369,6 +375,7 @@ describe("Image Tool - Edge Cases", () => {
       expect(mockExecuteSwiftCli).toHaveBeenCalledWith(
         expect.arrayContaining(["--path", pathWithPipe]),
         mockLogger,
+        expect.objectContaining({ timeout: expect.any(Number) })
       );
     });
 
@@ -393,6 +400,7 @@ describe("Image Tool - Edge Cases", () => {
       expect(mockExecuteSwiftCli).toHaveBeenCalledWith(
         expect.arrayContaining(["--path", pathWithColon]),
         mockLogger,
+        expect.objectContaining({ timeout: expect.any(Number) })
       );
     });
 
@@ -417,6 +425,7 @@ describe("Image Tool - Edge Cases", () => {
       expect(mockExecuteSwiftCli).toHaveBeenCalledWith(
         expect.arrayContaining(["--path", pathWithAsterisk]),
         mockLogger,
+        expect.objectContaining({ timeout: expect.any(Number) })
       );
     });
 
@@ -441,6 +450,7 @@ describe("Image Tool - Edge Cases", () => {
       expect(mockExecuteSwiftCli).toHaveBeenCalledWith(
         expect.arrayContaining(["--path", complexPath]),
         mockLogger,
+        expect.objectContaining({ timeout: expect.any(Number) })
       );
     });
 
@@ -465,6 +475,7 @@ describe("Image Tool - Edge Cases", () => {
       expect(mockExecuteSwiftCli).toHaveBeenCalledWith(
         expect.arrayContaining(["--path", pathWithSpaces]),
         mockLogger,
+        expect.objectContaining({ timeout: expect.any(Number) })
       );
     });
   });
diff --git a/tests/unit/tools/image.test.ts b/tests/unit/tools/image.test.ts
index 9dcf745..bcd2aa2 100644
--- a/tests/unit/tools/image.test.ts
+++ b/tests/unit/tools/image.test.ts
@@ -92,6 +92,7 @@ describe("Image Tool", () => {
       expect(mockExecuteSwiftCli).toHaveBeenCalledWith(
         expect.arrayContaining(["image", "--mode", "screen", "--path", MOCK_TEMP_IMAGE_DIR, "--format", "png"]),
         mockLogger,
+        expect.objectContaining({ timeout: expect.any(Number) })
       );
       
       // When format is omitted, it defaults to "png", not "data"
@@ -139,6 +140,7 @@ describe("Image Tool", () => {
       expect(mockExecuteSwiftCli).toHaveBeenCalledWith(
         expect.arrayContaining(["--format", "png"]),
         mockLogger,
+        expect.objectContaining({ timeout: expect.any(Number) })
       );
       
       // Should NOT return base64 data for screen captures
@@ -205,6 +207,7 @@ describe("Image Tool", () => {
       expect(mockExecuteSwiftCli).toHaveBeenCalledWith(
         expect.arrayContaining(["--path", userPath, "--format", "png"]),
         mockLogger,
+        expect.objectContaining({ timeout: expect.any(Number) })
       );
       expect(result.content).toEqual(
         expect.arrayContaining([
@@ -283,6 +286,7 @@ describe("Image Tool", () => {
       expect(mockExecuteSwiftCli).toHaveBeenCalledWith(
         expect.arrayContaining(["--mode", "screen", "--screen-index", "1"]),
         mockLogger,
+        expect.objectContaining({ timeout: expect.any(Number) })
       );
     });
 
@@ -310,10 +314,12 @@ describe("Image Tool", () => {
       expect(mockExecuteSwiftCli).toHaveBeenCalledWith(
         expect.arrayContaining(["--mode", "screen"]),
         mockLogger,
+        expect.objectContaining({ timeout: expect.any(Number) })
       );
       expect(mockExecuteSwiftCli).toHaveBeenCalledWith(
         expect.not.arrayContaining(["--screen-index"]),
         mockLogger,
+        expect.objectContaining({ timeout: expect.any(Number) })
       );
     });
 
@@ -343,6 +349,7 @@ describe("Image Tool", () => {
       expect(mockExecuteSwiftCli).toHaveBeenCalledWith(
         expect.arrayContaining(["--format", "png"]),
         mockLogger,
+        expect.objectContaining({ timeout: expect.any(Number) })
       );
     });
 
@@ -372,6 +379,7 @@ describe("Image Tool", () => {
       expect(mockExecuteSwiftCli).toHaveBeenCalledWith(
         expect.arrayContaining(["--format", "jpg"]),
         mockLogger,
+        expect.objectContaining({ timeout: expect.any(Number) })
       );
     });
 
@@ -398,6 +406,7 @@ describe("Image Tool", () => {
       expect(mockExecuteSwiftCli).toHaveBeenCalledWith(
         expect.arrayContaining(["--mode", "screen"]),
         mockLogger,
+        expect.objectContaining({ timeout: expect.any(Number) })
       );
     });
 
@@ -419,6 +428,7 @@ describe("Image Tool", () => {
       expect(mockExecuteSwiftCli).toHaveBeenCalledWith(
         expect.arrayContaining(["--app", "Safari", "--mode", "multi"]),
         mockLogger,
+        expect.objectContaining({ timeout: expect.any(Number) })
       );
     });
 
@@ -444,6 +454,7 @@ describe("Image Tool", () => {
           "--window-title", "Apple"
         ]),
         mockLogger,
+        expect.objectContaining({ timeout: expect.any(Number) })
       );
     });
 
@@ -469,6 +480,7 @@ describe("Image Tool", () => {
           "--window-index", "2"
         ]),
         mockLogger,
+        expect.objectContaining({ timeout: expect.any(Number) })
       );
     });
 
@@ -490,6 +502,7 @@ describe("Image Tool", () => {
       expect(mockExecuteSwiftCli).toHaveBeenCalledWith(
         expect.arrayContaining(["--capture-focus", "foreground"]),
         mockLogger,
+        expect.objectContaining({ timeout: expect.any(Number) })
       );
     });
 
@@ -511,6 +524,7 @@ describe("Image Tool", () => {
       expect(mockExecuteSwiftCli).toHaveBeenCalledWith(
         expect.arrayContaining(["--capture-focus", "auto"]),
         mockLogger,
+        expect.objectContaining({ timeout: expect.any(Number) })
       );
     });
 
@@ -532,6 +546,7 @@ describe("Image Tool", () => {
       expect(mockExecuteSwiftCli).toHaveBeenCalledWith(
         expect.arrayContaining(["--capture-focus", "background"]),
         mockLogger,
+        expect.objectContaining({ timeout: expect.any(Number) })
       );
     });
   });
@@ -574,6 +589,7 @@ describe("Image Tool", () => {
       expect(mockExecuteSwiftCli).toHaveBeenCalledWith(
         expect.arrayContaining(["--path", MOCK_TEMP_IMAGE_DIR]),
         mockLogger,
+        expect.objectContaining({ timeout: expect.any(Number) })
       );
       expect(mockPerformAutomaticAnalysis).toHaveBeenCalledWith(
         "base64dataforanalysis",
@@ -633,6 +649,7 @@ describe("Image Tool", () => {
       expect(mockExecuteSwiftCli).toHaveBeenCalledWith(
         expect.arrayContaining(["--path", USER_PATH, "--format", "jpg"]),
         mockLogger,
+        expect.objectContaining({ timeout: expect.any(Number) })
       );
       expect(mockPerformAutomaticAnalysis).toHaveBeenCalledWith(
         "base64dataforanalysis",
@@ -1170,6 +1187,7 @@ describe("Image Tool", () => {
       expect(mockExecuteSwiftCli).toHaveBeenCalledWith(
         expect.arrayContaining(["--format", "png"]),
         mockLogger,
+        expect.objectContaining({ timeout: expect.any(Number) })
       );
     });
 
@@ -1201,6 +1219,7 @@ describe("Image Tool", () => {
       expect(mockExecuteSwiftCli).toHaveBeenCalledWith(
         expect.arrayContaining(["--format", "png"]),
         mockLogger,
+        expect.objectContaining({ timeout: expect.any(Number) })
       );
     });
   });