@@ -138,7 +138,12 @@ import { validateAndFixToolResultIds } from "./validateToolResultIds"
 import { mergeConsecutiveApiMessages } from "./mergeConsecutiveApiMessages"
 import { prepareApiConversationMessage } from "./apiConversationHistory"
 import { shouldAddUserMessageToHistory } from "./messageCounting"
-import { decideMidStreamFailure, MAX_MID_STREAM_RETRIES, shouldRemoveMidStreamRetryMessage } from "./midStreamRetry"
+import {
+	decideMidStreamFailure,
+	MAX_MID_STREAM_RETRIES,
+	shouldRemoveMidStreamRetryMessage,
+	wasMidStreamRetryMessageAdded,
+} from "./midStreamRetry"
 import { type TaskExecutionContext } from "./providerHandoff"
 
 const MAX_EXPONENTIAL_BACKOFF_SECONDS = 600 // 10 minutes
@@ -2926,10 +2931,10 @@ export class Task extends EventEmitter<TaskEvents> implements TaskLike {
 			includeFileDetails: boolean
 			retryAttempt?: number
 			userMessageWasRemoved?: boolean // Track if user message was removed due to empty response
-			userMessageWasAdded: boolean
+			userMessageWasAdded?: boolean
 		}
 
-		const stack: StackItem[] = [{ userContent, includeFileDetails, retryAttempt: 0, userMessageWasAdded: false }]
+		const stack: StackItem[] = [{ userContent, includeFileDetails, retryAttempt: 0 }]
 
 		while (stack.length > 0) {
 			const currentItem = stack.pop()!
@@ -3068,7 +3073,7 @@ export class Task extends EventEmitter<TaskEvents> implements TaskLike {
 				isEmptyUserContent,
 				userMessageWasRemoved: currentItem.userMessageWasRemoved,
 			})
-			let { userMessageWasAdded } = currentItem
+			let userMessageWasAdded = wasMidStreamRetryMessageAdded(currentItem.userMessageWasAdded)
 			if (shouldAddUserMessage) {
 				await this.addToApiConversationHistory({ role: "user", content: finalUserContent })
 				this.messageCounts.user++
@@ -3708,7 +3713,6 @@ export class Task extends EventEmitter<TaskEvents> implements TaskLike {
 										// Stryker disable next-line BooleanLiteral: file details are already materialized in the persisted request being retried.
 										includeFileDetails: false,
 										retryAttempt: 0,
-										userMessageWasAdded: false,
 									})
 
 									// Continue to retry the request
@@ -4108,7 +4112,6 @@ export class Task extends EventEmitter<TaskEvents> implements TaskLike {
 						stack.push({
 							userContent: [...this.userMessageContent], // Create a copy to avoid mutation issues
 							includeFileDetails: false, // Subsequent iterations don't need file details
-							userMessageWasAdded: false,
 						})
 
 						// Add periodic yielding to prevent blocking
@@ -4176,7 +4179,6 @@ export class Task extends EventEmitter<TaskEvents> implements TaskLike {
 							includeFileDetails: false,
 							retryAttempt: (currentItem.retryAttempt ?? 0) + 1,
 							userMessageWasRemoved: removedCurrentUserMessage,
-							userMessageWasAdded: false,
 						})
 
 						// Continue to retry the request
@@ -4198,7 +4200,6 @@ export class Task extends EventEmitter<TaskEvents> implements TaskLike {
 								includeFileDetails: false,
 								retryAttempt: (currentItem.retryAttempt ?? 0) + 1,
 								userMessageWasRemoved: removedCurrentUserMessage,
-								userMessageWasAdded: false,
 							})
 
 							// Continue to retry the request
 
@@ -1,6 +1,11 @@
 import { describe, expect, it } from "vitest"
 
-import { decideMidStreamFailure, MAX_MID_STREAM_RETRIES, shouldRemoveMidStreamRetryMessage } from "../midStreamRetry"
+import {
+	decideMidStreamFailure,
+	MAX_MID_STREAM_RETRIES,
+	shouldRemoveMidStreamRetryMessage,
+	wasMidStreamRetryMessageAdded,
+} from "../midStreamRetry"
 
 describe("decideMidStreamFailure", () => {
 	it.each([0, 1, 2])("retries attempt %i", (attempt) => {
@@ -22,3 +27,13 @@ describe("shouldRemoveMidStreamRetryMessage", () => {
 		expect(shouldRemoveMidStreamRetryMessage(added, role)).toBe(expected)
 	})
 })
+
+describe("wasMidStreamRetryMessageAdded", () => {
+	it.each([
+		{ value: true, expected: true },
+		{ value: false, expected: false },
+		{ value: undefined, expected: false },
+	])("returns $expected for $value", ({ value, expected }) => {
+		expect(wasMidStreamRetryMessageAdded(value)).toBe(expected)
+	})
+})
@@ -9,3 +9,7 @@ export function decideMidStreamFailure(retryAttempt: number): MidStreamFailureDe
 export function shouldRemoveMidStreamRetryMessage(userMessageWasAdded: boolean, lastRole?: string): boolean {
 	return userMessageWasAdded && lastRole === "user"
 }
+
+export function wasMidStreamRetryMessageAdded(value?: boolean): boolean {
+	return value === true
+}
Original file line number	Diff line number	Diff line change
`@@ -9,3 +9,7 @@ export function decideMidStreamFailure(retryAttempt: number): MidStreamFailureDe`
`9`	`9`	`export function shouldRemoveMidStreamRetryMessage(userMessageWasAdded: boolean, lastRole?: string): boolean {`
`10`	`10`	`return userMessageWasAdded && lastRole === "user"`
`11`	`11`	`}`
	`12`	`+`
	`13`	`+export function wasMidStreamRetryMessageAdded(value?: boolean): boolean {`
	`14`	`+ return value === true`
	`15`	`+}`