diff --git a/src/tools/image.ts b/src/tools/image.ts
index c63483b..b9d98e3 100644
--- a/src/tools/image.ts
+++ b/src/tools/image.ts
@@ -92,6 +92,26 @@ export async function imageToolHandler(
       analysisAttempted = true;
       const analysisResults: Array<{ label: string; text: string }> = [];
 
+      // Helper function to generate descriptive labels for analysis
+      const getAnalysisLabel = (savedFile: SavedFile, isMultipleFiles: boolean): string => {
+        if (!isMultipleFiles) {
+          // For single files, use the item_label (app name or screen description)
+          return savedFile.item_label || "Unknown";
+        }
+        
+        // For multiple files, prefer window_title if available
+        if (savedFile.window_title) {
+          return `"${savedFile.window_title}"`;
+        }
+        
+        // Fall back to item_label with window index if available
+        if (savedFile.window_index !== undefined) {
+          return `${savedFile.item_label || "Unknown"} (Window ${savedFile.window_index + 1})`;
+        }
+        
+        return savedFile.item_label || "Unknown";
+      };
+
       const configuredProviders = parseAIProviders(
         process.env.PEEKABOO_AI_PROVIDERS || "",
       );
@@ -101,7 +121,10 @@ export async function imageToolHandler(
         logger.warn(analysisText);
       } else {
         // Iterate through all saved files for analysis
+        const isMultipleFiles = captureData.saved_files.length > 1;
         for (const savedFile of captureData.saved_files) {
+          const analysisLabel = getAnalysisLabel(savedFile, isMultipleFiles);
+          
           try {
             const imageBase64 = await readImageAsBase64(savedFile.path);
             logger.debug({ path: savedFile.path }, "Image read successfully for analysis.");
@@ -115,12 +138,12 @@ export async function imageToolHandler(
 
             if (analysisResult.error) {
               analysisResults.push({
-                label: savedFile.item_label || "Unknown",
+                label: analysisLabel,
                 text: analysisResult.error,
               });
             } else {
               analysisResults.push({
-                label: savedFile.item_label || "Unknown",
+                label: analysisLabel,
                 text: analysisResult.analysisText || "",
               });
               modelUsed = analysisResult.modelUsed;
@@ -133,7 +156,7 @@ export async function imageToolHandler(
               "Failed to read captured image for analysis",
             );
             analysisResults.push({
-              label: savedFile.item_label || "Unknown",
+              label: analysisLabel,
               text: `Analysis skipped: Failed to read captured image at ${savedFile.path}. Error: ${readError instanceof Error ? readError.message : "Unknown read error"}`,
             });
           }
diff --git a/tests/unit/tools/image.test.ts b/tests/unit/tools/image.test.ts
index 36e8e7f..2530a3c 100644
--- a/tests/unit/tools/image.test.ts
+++ b/tests/unit/tools/image.test.ts
@@ -741,6 +741,128 @@ describe("Image Tool", () => {
       // Verify that the temporary directory is no longer cleaned up (files preserved)
       expect(mockFsRm).not.toHaveBeenCalled();
     });
+
+    it("should use window titles for analysis labels when capturing multiple windows", async () => {
+      // Mock resolveImagePath to return a temporary directory path
+      mockResolveImagePath.mockResolvedValue({
+        effectivePath: MOCK_TEMP_IMAGE_DIR,
+        tempDirUsed: MOCK_TEMP_IMAGE_DIR,
+      });
+      
+      // Mock executeSwiftCli with two saved files that have window titles
+      const mockFile1: SavedFile = {
+        path: "/tmp/peekaboo-img-XXXXXX/chrome_window1.png",
+        mime_type: "image/png",
+        item_label: "Google Chrome",
+        window_title: "MCP Inspector",
+        window_index: 0,
+        window_id: 123,
+      };
+      const mockFile2: SavedFile = {
+        path: "/tmp/peekaboo-img-XXXXXX/chrome_window2.png", 
+        mime_type: "image/png",
+        item_label: "Google Chrome",
+        window_title: "(9) Home / X",
+        window_index: 1,
+        window_id: 124,
+      };
+      const mockResponse = {
+        success: true,
+        data: { saved_files: [mockFile1, mockFile2] },
+        messages: ["Captured 2 Chrome windows"],
+      };
+      mockExecuteSwiftCli.mockResolvedValue(mockResponse);
+      
+      // Mock readImageAsBase64 to return different base64 strings
+      mockReadImageAsBase64
+        .mockResolvedValueOnce("base64dataforwindow1")
+        .mockResolvedValueOnce("base64dataforwindow2");
+      
+      // Mock performAutomaticAnalysis to return different analysis for each call
+      mockPerformAutomaticAnalysis
+        .mockResolvedValueOnce({
+          analysisText: "This shows the MCP Inspector interface.",
+          modelUsed: MOCK_MODEL_USED,
+        })
+        .mockResolvedValueOnce({
+          analysisText: "This shows the X (Twitter) home page.",
+          modelUsed: MOCK_MODEL_USED,
+        });
+
+      // Call imageToolHandler with a question
+      const result = await imageToolHandler(
+        { question: "What is shown in each window?" },
+        mockContext,
+      );
+
+      // Verify the final analysis_text uses window titles instead of app names
+      expect(result.analysis_text).toBe(
+        'Analysis for "MCP Inspector":\nThis shows the MCP Inspector interface.\n\nAnalysis for "(9) Home / X":\nThis shows the X (Twitter) home page.'
+      );
+      
+      // Verify that the temporary directory is no longer cleaned up (files preserved)
+      expect(mockFsRm).not.toHaveBeenCalled();
+    });
+
+    it("should fallback to window index when no window title is available", async () => {
+      // Mock resolveImagePath to return a temporary directory path
+      mockResolveImagePath.mockResolvedValue({
+        effectivePath: MOCK_TEMP_IMAGE_DIR,
+        tempDirUsed: MOCK_TEMP_IMAGE_DIR,
+      });
+      
+      // Mock executeSwiftCli with two saved files without window titles
+      const mockFile1: SavedFile = {
+        path: "/tmp/peekaboo-img-XXXXXX/app_window1.png",
+        mime_type: "image/png",
+        item_label: "Some App",
+        window_index: 0,
+        window_id: 123,
+      };
+      const mockFile2: SavedFile = {
+        path: "/tmp/peekaboo-img-XXXXXX/app_window2.png", 
+        mime_type: "image/png",
+        item_label: "Some App",
+        window_index: 1,
+        window_id: 124,
+      };
+      const mockResponse = {
+        success: true,
+        data: { saved_files: [mockFile1, mockFile2] },
+        messages: ["Captured 2 app windows"],
+      };
+      mockExecuteSwiftCli.mockResolvedValue(mockResponse);
+      
+      // Mock readImageAsBase64 to return different base64 strings
+      mockReadImageAsBase64
+        .mockResolvedValueOnce("base64dataforwindow1")
+        .mockResolvedValueOnce("base64dataforwindow2");
+      
+      // Mock performAutomaticAnalysis to return different analysis for each call
+      mockPerformAutomaticAnalysis
+        .mockResolvedValueOnce({
+          analysisText: "Analysis for first window.",
+          modelUsed: MOCK_MODEL_USED,
+        })
+        .mockResolvedValueOnce({
+          analysisText: "Analysis for second window.",
+          modelUsed: MOCK_MODEL_USED,
+        });
+
+      // Call imageToolHandler with a question
+      const result = await imageToolHandler(
+        { question: "What is shown in each window?" },
+        mockContext,
+      );
+
+      // Verify the final analysis_text uses window index fallback
+      expect(result.analysis_text).toBe(
+        "Analysis for Some App (Window 1):\nAnalysis for first window.\n\nAnalysis for Some App (Window 2):\nAnalysis for second window."
+      );
+      
+      // Verify that the temporary directory is no longer cleaned up (files preserved)
+      expect(mockFsRm).not.toHaveBeenCalled();
+    });
   });
 
   describe("buildSwiftCliArgs", () => {