diff --git a/src/extension/chatSessions/vscode-node/copilotCLIChatSessions.ts b/src/extension/chatSessions/vscode-node/copilotCLIChatSessions.ts
index 8982dc62b..1b49a57d1 100644
--- a/src/extension/chatSessions/vscode-node/copilotCLIChatSessions.ts
+++ b/src/extension/chatSessions/vscode-node/copilotCLIChatSessions.ts
@@ -1262,13 +1262,13 @@ export class CopilotCLIChatSessionParticipant extends Disposable {
 		}
 	}
 
-	private static readonly _PR_DETECTION_RETRY_COUNT = 3;
+	private static readonly _PR_DETECTION_RETRY_COUNT = 5;
 	private static readonly _PR_DETECTION_INITIAL_DELAY_MS = 2_000;
 
 	private async handlePullRequestCreated(session: ICopilotCLISession): Promise<void> {
 		const sessionId = session.sessionId;
 		let prUrl = session.createdPullRequestUrl;
-		let prState = 'open';
+		let prState = '';
 
 		this.logService.debug(`[CopilotCLIChatSessionParticipant] handlePullRequestCreated for ${sessionId}: createdPullRequestUrl=${prUrl ?? 'none'}`);
 
@@ -1285,7 +1285,7 @@ export class CopilotCLIChatSessionParticipant extends Disposable {
 				this.logService.debug(`[CopilotCLIChatSessionParticipant] No PR URL from session, attempting retry detection for ${sessionId}, branch=${worktreeProperties.branchName}`);
 				const prResult = await this.detectPullRequestWithRetry(sessionId);
 				prUrl = prResult?.url;
-				prState = prResult?.state ?? 'open';
+				prState = prResult?.state ?? prResult?.url ? 'open' : '';
 			} else {
 				this.logService.debug(`[CopilotCLIChatSessionParticipant] Skipping retry detection for ${sessionId}: branch=${worktreeProperties.branchName ?? 'none'}, repoPath=${!!worktreeProperties.repositoryPath}`);
 			}
diff --git a/src/extension/chatSessions/vscode-node/copilotCLIChatSessionsContribution.ts b/src/extension/chatSessions/vscode-node/copilotCLIChatSessionsContribution.ts
index c5d84c0c3..04a025c07 100644
--- a/src/extension/chatSessions/vscode-node/copilotCLIChatSessionsContribution.ts
+++ b/src/extension/chatSessions/vscode-node/copilotCLIChatSessionsContribution.ts
@@ -1535,13 +1535,13 @@ export class CopilotCLIChatSessionParticipant extends Disposable {
 		}
 	}
 
-	private static readonly _PR_DETECTION_RETRY_COUNT = 3;
+	private static readonly _PR_DETECTION_RETRY_COUNT = 5;
 	private static readonly _PR_DETECTION_INITIAL_DELAY_MS = 2_000;
 
 	private async handlePullRequestCreated(session: ICopilotCLISession): Promise<void> {
 		const sessionId = session.sessionId;
 		let prUrl = session.createdPullRequestUrl;
-		let prState = 'open';
+		let prState = '';
 
 		this.logService.debug(`[CopilotCLIChatSessionParticipant] handlePullRequestCreated for ${sessionId}: createdPullRequestUrl=${prUrl ?? 'none'}`);
 
@@ -1559,7 +1559,7 @@ export class CopilotCLIChatSessionParticipant extends Disposable {
 				this.logService.debug(`[CopilotCLIChatSessionParticipant] No PR URL from session, attempting retry detection for ${sessionId}, branch=${worktreeProperties.branchName}`);
 				const prResult = await this.detectPullRequestWithRetry(sessionId);
 				prUrl = prResult?.url;
-				prState = prResult?.state ?? 'open';
+				prState = prResult?.state ?? prUrl ? 'open' : '';
 			} else {
 				this.logService.debug(`[CopilotCLIChatSessionParticipant] Skipping retry detection for ${sessionId}: branch=${worktreeProperties.branchName ?? 'none'}, repoPath=${!!worktreeProperties.repositoryPath}`);
 			}
diff --git a/src/extension/chatSessions/vscode-node/test/copilotCLIChatSessionParticipant.spec.ts b/src/extension/chatSessions/vscode-node/test/copilotCLIChatSessionParticipant.spec.ts
index 9aa15e597..d684a64ec 100644
--- a/src/extension/chatSessions/vscode-node/test/copilotCLIChatSessionParticipant.spec.ts
+++ b/src/extension/chatSessions/vscode-node/test/copilotCLIChatSessionParticipant.spec.ts
@@ -2097,8 +2097,8 @@ describe('CopilotCLIChatSessionParticipant.handleRequest', () => {
 			await vi.runAllTimersAsync();
 			await handlerPromise;
 
-			// 3 attempts total (after 2s, 4s, and 8s delays)
-			expect(findPr).toHaveBeenCalledTimes(3);
+			// 5 attempts total (after 2s, 4s, 8s, 16s, and 32s delays)
+			expect(findPr).toHaveBeenCalledTimes(5);
 			// Should NOT have persisted any PR URL since all attempts failed
 			const setPropsCallsWithPrUrl = (worktree.setWorktreeProperties as ReturnType<typeof vi.fn>).mock.calls
 				.filter((args: unknown[]) => (args[1] as { pullRequestUrl?: string })?.pullRequestUrl !== undefined);