diff --git a/CHANGELOG.md b/CHANGELOG.md
index 784301a..061cc43 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -16,6 +16,10 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 - Invalid format values now automatically fall back to PNG instead of returning an error
   - Empty strings, null values, and unrecognized format values are converted to PNG
   - This provides a better user experience by gracefully handling invalid inputs
+- Enhanced error messages for ambiguous application identifiers
+  - When multiple applications match an identifier (e.g., "C" matches Calendar, Console, and Cursor), the error message now lists all matching applications with their bundle IDs
+  - This helps users quickly identify the correct application name to use
+  - Applies to both `image` and `list` tools
 
 ## [1.0.0-beta.18] - 2025-06-08
 
diff --git a/src/tools/image.ts b/src/tools/image.ts
index 82f0f2d..8b0be60 100644
--- a/src/tools/image.ts
+++ b/src/tools/image.ts
@@ -63,11 +63,17 @@ export async function imageToolHandler(
         { error: swiftResponse.error },
         "Swift CLI returned error for image capture",
       );
+      const errorMessage = swiftResponse.error?.message || "Unknown error";
+      const errorDetails = swiftResponse.error?.details;
+      const fullErrorMessage = errorDetails 
+        ? `${errorMessage}\n${errorDetails}`
+        : errorMessage;
+        
       return {
         content: [
           {
             type: "text",
-            text: `Image capture failed: ${swiftResponse.error?.message || "Unknown error"}`,
+            text: `Image capture failed: ${fullErrorMessage}`,
           },
         ],
         isError: true,
diff --git a/src/tools/list.ts b/src/tools/list.ts
index 33fd4d9..94de8cc 100644
--- a/src/tools/list.ts
+++ b/src/tools/list.ts
@@ -119,11 +119,17 @@ export async function listToolHandler(
 
     if (!swiftResponse.success) {
       logger.error({ error: swiftResponse.error }, "Swift CLI returned error");
+      const errorMessage = swiftResponse.error?.message || "Unknown error";
+      const errorDetails = swiftResponse.error?.details;
+      const fullErrorMessage = errorDetails 
+        ? `${errorMessage}\n${errorDetails}`
+        : errorMessage;
+        
       return {
         content: [
           {
             type: "text" as const,
-            text: `List operation failed: ${swiftResponse.error?.message || "Unknown error"}`,
+            text: `List operation failed: ${fullErrorMessage}`,
           },
         ],
         isError: true,
diff --git a/tests/unit/tools/image.test.ts b/tests/unit/tools/image.test.ts
index 694dde7..39c4581 100644
--- a/tests/unit/tools/image.test.ts
+++ b/tests/unit/tools/image.test.ts
@@ -1142,4 +1142,62 @@ describe("Image Tool", () => {
       );
     });
   });
+
+  describe("imageToolHandler - Error message handling", () => {
+    it("should include error details for ambiguous app identifier", async () => {
+      // Mock resolveImagePath
+      mockResolveImagePath.mockResolvedValue({
+        effectivePath: MOCK_TEMP_IMAGE_DIR,
+        tempDirUsed: MOCK_TEMP_IMAGE_DIR,
+      });
+      
+      // Mock Swift CLI returning ambiguous app error with details
+      mockExecuteSwiftCli.mockResolvedValue({
+        success: false,
+        error: {
+          message: "Multiple applications match identifier 'C'. Please be more specific.",
+          code: "AMBIGUOUS_APP_IDENTIFIER",
+          details: "Matches found: Calendar (com.apple.iCal), Console (com.apple.Console), Cursor (com.todesktop.230313mzl4w4u92)"
+        }
+      });
+
+      const result = await imageToolHandler(
+        { app_target: "C" },
+        mockContext,
+      );
+
+      expect(result.isError).toBe(true);
+      expect(result.content[0].type).toBe("text");
+      // Should include both the main message and the details
+      expect(result.content[0].text).toContain("Multiple applications match identifier 'C'");
+      expect(result.content[0].text).toContain("Matches found: Calendar (com.apple.iCal), Console (com.apple.Console), Cursor (com.todesktop.230313mzl4w4u92)");
+    });
+
+    it("should handle errors without details gracefully", async () => {
+      // Mock resolveImagePath
+      mockResolveImagePath.mockResolvedValue({
+        effectivePath: MOCK_TEMP_IMAGE_DIR,
+        tempDirUsed: MOCK_TEMP_IMAGE_DIR,
+      });
+      
+      // Mock Swift CLI returning error without details
+      mockExecuteSwiftCli.mockResolvedValue({
+        success: false,
+        error: {
+          message: "Application not found",
+          code: "APP_NOT_FOUND"
+        }
+      });
+
+      const result = await imageToolHandler(
+        { app_target: "NonExistent" },
+        mockContext,
+      );
+
+      expect(result.isError).toBe(true);
+      expect(result.content[0].type).toBe("text");
+      // Should only include the main message
+      expect(result.content[0].text).toBe("Image capture failed: Application not found");
+    });
+  });
 });
\ No newline at end of file
diff --git a/tests/unit/tools/list.test.ts b/tests/unit/tools/list.test.ts
index fbba125..bf143f9 100644
--- a/tests/unit/tools/list.test.ts
+++ b/tests/unit/tools/list.test.ts
@@ -288,7 +288,7 @@ describe("List Tool", () => {
       // Assert
       expect(result.isError).toBe(true);
       expect(result.content[0].text).toBe(
-        "List operation failed: The specified application ('Ciursor') is not running or could not be found."
+        "List operation failed: The specified application ('Ciursor') is not running or could not be found.\nError: Application with name 'Ciursor' not found."
       );
     });
 
@@ -865,4 +865,32 @@ describe("List Tool", () => {
         }
     });
   });
+
+  describe("listToolHandler - Error message handling", () => {
+    it("should include error details for ambiguous app identifier", async () => {
+      // Mock Swift CLI returning ambiguous app error with details
+      mockExecuteSwiftCli.mockResolvedValue({
+        success: false,
+        error: {
+          message: "Multiple applications match identifier 'C'. Please be more specific.",
+          code: "AMBIGUOUS_APP_IDENTIFIER",
+          details: "Matches found: Calendar (com.apple.iCal), Console (com.apple.Console), Cursor (com.todesktop.230313mzl4w4u92)"
+        }
+      });
+
+      const result = await listToolHandler(
+        { 
+          item_type: "application_windows",
+          app: "C" 
+        },
+        mockContext,
+      );
+
+      expect(result.isError).toBe(true);
+      expect(result.content[0].type).toBe("text");
+      // Should include both the main message and the details
+      expect(result.content[0].text).toContain("Multiple applications match identifier 'C'");
+      expect(result.content[0].text).toContain("Matches found: Calendar (com.apple.iCal), Console (com.apple.Console), Cursor (com.todesktop.230313mzl4w4u92)");
+    });
+  });
 });