diff --git a/docs/AGENTS.md b/docs/AGENTS.md
index 496e283a4..1eb92520f 100644
--- a/docs/AGENTS.md
+++ b/docs/AGENTS.md
@@ -152,4 +152,5 @@ gh pr view <number> --json mergeable,mergeStateStatus | jq '.'
 
 ## Mode: Plan
 
+- When Plan Mode is requested, assume the user wants the actual completed plan; do not merely describe how you would devise one.
 - Attach a net LoC estimate (product code only) to each recommended approach.
diff --git a/src/browser/utils/messages/StreamingMessageAggregator.ts b/src/browser/utils/messages/StreamingMessageAggregator.ts
index fcdd02d91..e0d1193e1 100644
--- a/src/browser/utils/messages/StreamingMessageAggregator.ts
+++ b/src/browser/utils/messages/StreamingMessageAggregator.ts
@@ -96,6 +96,8 @@ export class StreamingMessageAggregator {
   // Track when we're waiting for stream-start after user message
   // Prevents retry barrier flash during normal send flow
   // Stores timestamp of when user message was sent (null = no pending stream)
+  // IMPORTANT: We intentionally keep this timestamp until a stream actually starts
+  // (or the user retries) so retry UI/backoff logic doesn't misfire on send failures.
   private pendingStreamStartTime: number | null = null;
 
   // Workspace creation timestamp (used for recency calculation)
diff --git a/src/browser/utils/messages/retryEligibility.test.ts b/src/browser/utils/messages/retryEligibility.test.ts
index fb8d1be51..403f1488a 100644
--- a/src/browser/utils/messages/retryEligibility.test.ts
+++ b/src/browser/utils/messages/retryEligibility.test.ts
@@ -3,6 +3,7 @@ import {
   hasInterruptedStream,
   isEligibleForAutoRetry,
   isNonRetryableSendError,
+  PENDING_STREAM_START_GRACE_PERIOD_MS,
 } from "./retryEligibility";
 import type { DisplayedMessage } from "@/common/types/message";
 import type { SendMessageError } from "@/common/types/errors";
@@ -165,7 +166,7 @@ describe("hasInterruptedStream", () => {
     expect(hasInterruptedStream(messages, null)).toBe(true);
   });
 
-  it("returns false when message was sent very recently (< 3s)", () => {
+  it("returns false when message was sent very recently (within grace period)", () => {
     const messages: DisplayedMessage[] = [
       {
         type: "user",
@@ -194,8 +195,8 @@ describe("hasInterruptedStream", () => {
         historySequence: 3,
       },
     ];
-    // Message sent 1 second ago - still within 3s window
-    const recentTimestamp = Date.now() - 1000;
+    // Message sent 1 second ago - still within grace window
+    const recentTimestamp = Date.now() - (PENDING_STREAM_START_GRACE_PERIOD_MS - 1000);
     expect(hasInterruptedStream(messages, recentTimestamp)).toBe(false);
   });
 
@@ -212,7 +213,7 @@ describe("hasInterruptedStream", () => {
     expect(hasInterruptedStream(messages, null)).toBe(true);
   });
 
-  it("returns false when user message just sent (< 3s ago)", () => {
+  it("returns false when user message just sent (within grace period)", () => {
     const messages: DisplayedMessage[] = [
       {
         type: "user",
@@ -222,11 +223,11 @@ describe("hasInterruptedStream", () => {
         historySequence: 1,
       },
     ];
-    const justSent = Date.now() - 500; // 0.5s ago
+    const justSent = Date.now() - (PENDING_STREAM_START_GRACE_PERIOD_MS - 500);
     expect(hasInterruptedStream(messages, justSent)).toBe(false);
   });
 
-  it("returns true when message sent over 3s ago (stream likely hung)", () => {
+  it("returns true when message sent beyond grace period (stream likely hung)", () => {
     const messages: DisplayedMessage[] = [
       {
         type: "user",
@@ -236,7 +237,7 @@ describe("hasInterruptedStream", () => {
         historySequence: 1,
       },
     ];
-    const longAgo = Date.now() - 4000; // 4s ago - past 3s threshold
+    const longAgo = Date.now() - (PENDING_STREAM_START_GRACE_PERIOD_MS + 1000);
     expect(hasInterruptedStream(messages, longAgo)).toBe(true);
   });
 
@@ -545,7 +546,7 @@ describe("isEligibleForAutoRetry", () => {
       expect(isEligibleForAutoRetry(messages, null)).toBe(true);
     });
 
-    it("returns false when user message sent very recently (< 3s)", () => {
+    it("returns false when user message sent very recently (within grace period)", () => {
       const messages: DisplayedMessage[] = [
         {
           type: "user",
@@ -555,7 +556,7 @@ describe("isEligibleForAutoRetry", () => {
           historySequence: 1,
         },
       ];
-      const justSent = Date.now() - 500; // 0.5s ago
+      const justSent = Date.now() - (PENDING_STREAM_START_GRACE_PERIOD_MS - 500);
       expect(isEligibleForAutoRetry(messages, justSent)).toBe(false);
     });
   });
diff --git a/src/browser/utils/messages/retryEligibility.ts b/src/browser/utils/messages/retryEligibility.ts
index 3d5f6fff2..eed8ec69f 100644
--- a/src/browser/utils/messages/retryEligibility.ts
+++ b/src/browser/utils/messages/retryEligibility.ts
@@ -18,6 +18,8 @@ declare global {
   }
 }
 
+export const PENDING_STREAM_START_GRACE_PERIOD_MS = 15000; // 15 seconds
+
 /**
  * Check if the debug flag to force all errors to be retryable is enabled
  */
@@ -69,7 +71,7 @@ export function isNonRetryableSendError(error: SendMessageError): boolean {
  * 3. Last message is a user message (indicating we sent it but never got a response)
  *    - This handles app restarts during slow model responses (models can take 30-60s to first token)
  *    - User messages are only at the end when response hasn't started/completed
- *    - EXCEPT: Not if recently sent (<3s ago) - prevents flash during normal send flow
+ *    - EXCEPT: Not if recently sent (within PENDING_STREAM_START_GRACE_PERIOD_MS) - prevents flash during normal send flow
  */
 export function hasInterruptedStream(
   messages: DisplayedMessage[],
@@ -77,12 +79,12 @@ export function hasInterruptedStream(
 ): boolean {
   if (messages.length === 0) return false;
 
-  // Don't show retry barrier if user message was sent very recently (< 3s)
+  // Don't show retry barrier if user message was sent very recently (within the grace period)
   // This prevents flash during normal send flow while stream-start event arrives
-  // After 3s, we assume something is wrong and show the barrier
+  // After the grace period, assume something is wrong and show the barrier
   if (pendingStreamStartTime !== null) {
     const elapsed = Date.now() - pendingStreamStartTime;
-    if (elapsed < 3000) return false;
+    if (elapsed < PENDING_STREAM_START_GRACE_PERIOD_MS) return false;
   }
 
   const lastMessage = messages[messages.length - 1];