diff --git a/src/gadgets/pm/core/postComment.ts b/src/gadgets/pm/core/postComment.ts
index 467a6f13..bc244037 100644
--- a/src/gadgets/pm/core/postComment.ts
+++ b/src/gadgets/pm/core/postComment.ts
@@ -1,5 +1,6 @@
 import { clearProgressCommentId, readProgressCommentId } from '../../../backends/progressState.js';
 import { getPMProvider } from '../../../pm/index.js';
+import { logger } from '../../../utils/logging.js';
 
 export async function postComment(workItemId: string, text: string): Promise<string> {
 	try {
@@ -12,8 +13,13 @@ export async function postComment(workItemId: string, text: string): Promise<str
 				await provider.updateComment(workItemId, progressState.commentId, text);
 				clearProgressCommentId();
 				return 'Comment posted successfully';
-			} catch {
+			} catch (error) {
 				// Fall back to creating a new comment if update fails
+				logger.warn('Failed to update progress comment, creating new one', {
+					workItemId,
+					commentId: progressState.commentId,
+					error: error instanceof Error ? error.message : String(error),
+				});
 				clearProgressCommentId();
 			}
 		}
diff --git a/tests/unit/gadgets/pm/core/postComment.test.ts b/tests/unit/gadgets/pm/core/postComment.test.ts
index 10c737e5..21bf458c 100644
--- a/tests/unit/gadgets/pm/core/postComment.test.ts
+++ b/tests/unit/gadgets/pm/core/postComment.test.ts
@@ -13,14 +13,22 @@ vi.mock('../../../../../src/backends/progressState.js', () => ({
 	clearProgressCommentId: vi.fn(),
 }));
 
+vi.mock('../../../../../src/utils/logging.js', () => ({
+	logger: {
+		warn: vi.fn(),
+	},
+}));
+
 import {
 	clearProgressCommentId,
 	readProgressCommentId,
 } from '../../../../../src/backends/progressState.js';
 import { postComment } from '../../../../../src/gadgets/pm/core/postComment.js';
+import { logger } from '../../../../../src/utils/logging.js';
 
 const mockReadProgressCommentId = vi.mocked(readProgressCommentId);
 const mockClearProgressCommentId = vi.mocked(clearProgressCommentId);
+const mockLogger = vi.mocked(logger);
 
 beforeEach(() => {
 	mockReadProgressCommentId.mockReturnValue(null);
@@ -103,6 +111,14 @@ describe('postComment', () => {
 				'comment-42',
 				'Final summary',
 			);
+			expect(mockLogger.warn).toHaveBeenCalledWith(
+				'Failed to update progress comment, creating new one',
+				expect.objectContaining({
+					workItemId: 'item1',
+					commentId: 'comment-42',
+					error: 'Comment not found',
+				}),
+			);
 			expect(mockProvider.addComment).toHaveBeenCalledWith('item1', 'Final summary');
 			expect(mockClearProgressCommentId).toHaveBeenCalled();
 			expect(result).toBe('Comment posted successfully');