diff --git a/src/core/assistant-message/__tests__/askApproval.test.ts b/src/core/assistant-message/__tests__/askApproval.test.ts
new file mode 100644
index 0000000000..1d4ad19174
--- /dev/null
+++ b/src/core/assistant-message/__tests__/askApproval.test.ts
@@ -0,0 +1,212 @@
+import { describe, it, expect, vi, beforeEach } from "vitest"
+import { Anthropic } from "@anthropic-ai/sdk"
+
+// Create a simplified test that focuses on the askApproval function behavior
+describe("askApproval - User Feedback Preservation", () => {
+	let mockTask: any
+	let askApproval: any
+
+	beforeEach(() => {
+		vi.clearAllMocks()
+
+		mockTask = {
+			ask: vi.fn(),
+			say: vi.fn(),
+			addToApiConversationHistory: vi.fn(),
+			didRejectTool: false,
+		}
+
+		// Extract the askApproval function logic for testing
+		askApproval = async (type: string, partialMessage?: string, progressStatus?: any, isProtected?: boolean) => {
+			const { response, text, images } = await mockTask.ask(
+				type,
+				partialMessage,
+				false,
+				progressStatus,
+				isProtected || false,
+			)
+
+			if (response !== "yesButtonClicked") {
+				// Handle both messageResponse and noButtonClicked with text.
+				if (text) {
+					await mockTask.say("user_feedback", text, images)
+
+					// Add user feedback to API conversation history to preserve context
+					const userContent: Anthropic.Messages.ContentBlockParam[] = [
+						{ type: "text", text: `[User feedback during tool validation]: ${text}` },
+					]
+					if (images && images.length > 0) {
+						// Mock formatResponse.imageBlocks
+						userContent.push(
+							...images.map((img: string) => ({
+								type: "image",
+								source: {
+									type: "base64",
+									media_type: "image/jpeg",
+									data: img,
+								},
+							})),
+						)
+					}
+					await mockTask.addToApiConversationHistory({ role: "user", content: userContent })
+				}
+				mockTask.didRejectTool = true
+				return false
+			}
+
+			// Handle yesButtonClicked with text.
+			if (text) {
+				await mockTask.say("user_feedback", text, images)
+
+				// Add user feedback to API conversation history to preserve context
+				const userContent: Anthropic.Messages.ContentBlockParam[] = [
+					{ type: "text", text: `[User feedback during tool validation]: ${text}` },
+				]
+				if (images && images.length > 0) {
+					// Mock formatResponse.imageBlocks
+					userContent.push(
+						...images.map((img: string) => ({
+							type: "image",
+							source: {
+								type: "base64",
+								media_type: "image/jpeg",
+								data: img,
+							},
+						})),
+					)
+				}
+				await mockTask.addToApiConversationHistory({ role: "user", content: userContent })
+			}
+
+			return true
+		}
+	})
+
+	it("should preserve user feedback in API conversation history when tool is approved with feedback", async () => {
+		// Mock user providing feedback when approving tool
+		const mockAskResponse = {
+			response: "yesButtonClicked" as const,
+			text: "Please read the entire file carefully",
+			images: ["image1.jpg"],
+		}
+		mockTask.ask.mockResolvedValue(mockAskResponse)
+
+		// Execute
+		const result = await askApproval("tool", "test message")
+
+		// Verify result
+		expect(result).toBe(true)
+
+		// Verify that user feedback was added to API conversation history
+		expect(mockTask.addToApiConversationHistory).toHaveBeenCalledWith({
+			role: "user",
+			content: [
+				{
+					type: "text",
+					text: "[User feedback during tool validation]: Please read the entire file carefully",
+				},
+				{
+					type: "image",
+					source: {
+						type: "base64",
+						media_type: "image/jpeg",
+						data: "image1.jpg",
+					},
+				},
+			],
+		})
+
+		// Verify that user feedback was also displayed in UI
+		expect(mockTask.say).toHaveBeenCalledWith("user_feedback", "Please read the entire file carefully", [
+			"image1.jpg",
+		])
+	})
+
+	it("should preserve user feedback in API conversation history when tool is rejected with feedback", async () => {
+		// Mock user providing feedback when rejecting tool
+		const mockAskResponse = {
+			response: "noButtonClicked" as const,
+			text: "Don't write to that file, use a different path",
+			images: undefined,
+		}
+		mockTask.ask.mockResolvedValue(mockAskResponse)
+
+		// Execute
+		const result = await askApproval("tool", "test message")
+
+		// Verify result
+		expect(result).toBe(false)
+		expect(mockTask.didRejectTool).toBe(true)
+
+		// Verify that user feedback was added to API conversation history
+		expect(mockTask.addToApiConversationHistory).toHaveBeenCalledWith({
+			role: "user",
+			content: [
+				{
+					type: "text",
+					text: "[User feedback during tool validation]: Don't write to that file, use a different path",
+				},
+			],
+		})
+
+		// Verify that user feedback was also displayed in UI
+		expect(mockTask.say).toHaveBeenCalledWith(
+			"user_feedback",
+			"Don't write to that file, use a different path",
+			undefined,
+		)
+	})
+
+	it("should not add to API conversation history when user approves without feedback", async () => {
+		// Mock user approving without feedback
+		const mockAskResponse = {
+			response: "yesButtonClicked" as const,
+			text: undefined,
+			images: undefined,
+		}
+		mockTask.ask.mockResolvedValue(mockAskResponse)
+
+		// Execute
+		const result = await askApproval("tool", "test message")
+
+		// Verify result
+		expect(result).toBe(true)
+
+		// Verify that no additional API conversation history was added
+		expect(mockTask.addToApiConversationHistory).not.toHaveBeenCalled()
+
+		// Verify that no user feedback was displayed in UI
+		expect(mockTask.say).not.toHaveBeenCalledWith("user_feedback", expect.anything(), expect.anything())
+	})
+
+	it("should handle messageResponse type with feedback", async () => {
+		// Mock user providing messageResponse with feedback
+		const mockAskResponse = {
+			response: "messageResponse" as const,
+			text: "Use ls -la --color=always instead",
+			images: undefined,
+		}
+		mockTask.ask.mockResolvedValue(mockAskResponse)
+
+		// Execute
+		const result = await askApproval("tool", "test message")
+
+		// Verify result
+		expect(result).toBe(false)
+		expect(mockTask.didRejectTool).toBe(true)
+
+		// Verify that user feedback was added to API conversation history
+		expect(mockTask.addToApiConversationHistory).toHaveBeenCalledWith({
+			role: "user",
+			content: [
+				{
+					type: "text",
+					text: "[User feedback during tool validation]: Use ls -la --color=always instead",
+				},
+			],
+		})
+
+		// Verify that user feedback was also displayed in UI
+		expect(mockTask.say).toHaveBeenCalledWith("user_feedback", "Use ls -la --color=always instead", undefined)
+	})
+})
diff --git a/src/core/assistant-message/presentAssistantMessage.ts b/src/core/assistant-message/presentAssistantMessage.ts
index 21c973ab50..9e685180aa 100644
--- a/src/core/assistant-message/presentAssistantMessage.ts
+++ b/src/core/assistant-message/presentAssistantMessage.ts
@@ -1,5 +1,6 @@
 import cloneDeep from "clone-deep"
 import { serializeError } from "serialize-error"
+import { Anthropic } from "@anthropic-ai/sdk"
 
 import type { ToolName, ClineAsk, ToolProgressStatus } from "@roo-code/types"
 import { TelemetryService } from "@roo-code/telemetry"
@@ -275,6 +276,16 @@ export async function presentAssistantMessage(cline: Task) {
 					// Handle both messageResponse and noButtonClicked with text.
 					if (text) {
 						await cline.say("user_feedback", text, images)
+
+						// Add user feedback to API conversation history to preserve context
+						const userContent: Anthropic.Messages.ContentBlockParam[] = [
+							{ type: "text", text: `[User feedback during tool validation]: ${text}` },
+						]
+						if (images && images.length > 0) {
+							userContent.push(...formatResponse.imageBlocks(images))
+						}
+						await cline.addToApiConversationHistory({ role: "user", content: userContent })
+
 						pushToolResult(formatResponse.toolResult(formatResponse.toolDeniedWithFeedback(text), images))
 					} else {
 						pushToolResult(formatResponse.toolDenied())
@@ -286,7 +297,15 @@ export async function presentAssistantMessage(cline: Task) {
 				// Handle yesButtonClicked with text.
 				if (text) {
 					await cline.say("user_feedback", text, images)
-					pushToolResult(formatResponse.toolResult(formatResponse.toolApprovedWithFeedback(text), images))
+
+					// Add user feedback to API conversation history to preserve context
+					const userContent: Anthropic.Messages.ContentBlockParam[] = [
+						{ type: "text", text: `[User feedback during tool validation]: ${text}` },
+					]
+					if (images && images.length > 0) {
+						userContent.push(...formatResponse.imageBlocks(images))
+					}
+					await cline.addToApiConversationHistory({ role: "user", content: userContent })
 				}
 
 				return true
diff --git a/src/core/task/Task.ts b/src/core/task/Task.ts
index 46da7485ed..f568933864 100644
--- a/src/core/task/Task.ts
+++ b/src/core/task/Task.ts
@@ -318,7 +318,7 @@ export class Task extends EventEmitter<ClineEvents> {
 		return readApiMessages({ taskId: this.taskId, globalStoragePath: this.globalStoragePath })
 	}
 
-	private async addToApiConversationHistory(message: Anthropic.MessageParam) {
+	public async addToApiConversationHistory(message: Anthropic.MessageParam) {
 		const messageWithTs = { ...message, ts: Date.now() }
 		this.apiConversationHistory.push(messageWithTs)
 		await this.saveApiConversationHistory()