diff --git a/src/core/Cline.ts b/src/core/Cline.ts
index 4bfcf59520..acecbd4fe6 100644
--- a/src/core/Cline.ts
+++ b/src/core/Cline.ts
@@ -1539,33 +1539,44 @@ export class Cline {
 					this.didAlreadyUseTool = true
 				}
 
+				// The user can approve, reject, or provide feedback (rejection). However the user may also send a message along with an approval, in which case we add a separate user message with this feedback.
+				const pushAdditionalToolFeedback = (feedback?: string, images?: string[]) => {
+					if (!feedback && !images) {
+						return
+					}
+					const content = formatResponse.toolResult(
+						`The user provided the following feedback:\n<feedback>\n${feedback}\n</feedback>`,
+						images,
+					)
+					if (typeof content === "string") {
+						this.userMessageContent.push({
+							type: "text",
+							text: content,
+						})
+					} else {
+						this.userMessageContent.push(...content)
+					}
+				}
+
 				const askApproval = async (type: ClineAsk, partialMessage?: string) => {
 					const { response, text, images } = await this.ask(type, partialMessage, false)
 					if (response !== "yesButtonClicked") {
-						// User did NOT approve (rejected)
-						if (response === "messageResponse") {
-							// Rejection WITH feedback
-							await this.say("user_feedback", text, images)
-							pushToolResult(formatResponse.toolResult(formatResponse.toolDeniedWithFeedback(text), images))
-
-							this.didRejectTool = true
-							return false
-						}
-						// Rejection WITHOUT explicit feedback
+						// User pressed reject button or responded with a message, which we treat as a rejection
 						pushToolResult(formatResponse.toolDenied())
-
+						if (text || images?.length) {
+							pushAdditionalToolFeedback(text, images)
+							await this.say("user_feedback", text, images)
+						}
 						this.didRejectTool = true // Prevent further tool uses in this message
 						return false
+					} else {
+						// User hit the approve button, and may have provided feedback
+						if (text || images?.length) {
+							pushAdditionalToolFeedback(text, images)
+							await this.say("user_feedback", text, images)
+						}
+						return true
 					}
-
-					// Handle yesButtonClicked with text (Acceptance WITH feedback)
-					if (text) {
-						await this.say("user_feedback", text, images)
-						pushToolResult(formatResponse.toolResult(formatResponse.toolApprovedWithFeedback(text), images)) // Structured feedback to model on approval
-					}
-
-					// User approved without feedback
-					return true
 				}
 
 				const showNotificationForApprovalIfAutoApprovalEnabled = (message: string) => {
@@ -1804,37 +1815,23 @@ export class Cline {
 									let didApprove = true
 									const { response, text, images } = await this.ask("tool", completeMessage, false)
 									if (response !== "yesButtonClicked") {
-										// User did NOT approve (rejected)
-
+										// User either sent a message or pressed reject button
 										// TODO: add similar context for other tool denial responses, to emphasize ie that a command was not run
 										const fileDeniedNote = fileExists
 											? "The file was not updated, and maintains its original contents."
 											: "The file was not created."
-										if (response === "messageResponse") {
-											// Rejection WITH feedback
+										pushToolResult(`The user denied this operation. ${fileDeniedNote}`)
+										if (text || images?.length) {
+											pushAdditionalToolFeedback(text, images)
 											await this.say("user_feedback", text, images)
-											pushToolResult(
-												formatResponse.toolResult(
-													`The user denied this operation. ${fileDeniedNote}\nThe user provided the following feedback:\n<feedback>\n${text}\n</feedback>`,
-													images,
-												),
-											)
-											this.didRejectTool = true
-											didApprove = false
-										} else {
-											pushToolResult(`The user denied this operation. ${fileDeniedNote}`)
-											this.didRejectTool = true
-											didApprove = false
 										}
+										this.didRejectTool = true
+										didApprove = false
 									} else {
-										// User approved
-
-										// Handle yesButtonClicked with text (Acceptance WITH feedback)
-										if (text) {
+										// User hit the approve button, and may have provided feedback
+										if (text || images?.length) {
+											pushAdditionalToolFeedback(text, images)
 											await this.say("user_feedback", text, images)
-											pushToolResult(
-												formatResponse.toolResult(formatResponse.toolApprovedWithFeedback(text), images),
-											)
 										}
 									}
 
diff --git a/src/core/prompts/responses.ts b/src/core/prompts/responses.ts
index 8a14acc02b..bf5db6bbe7 100644
--- a/src/core/prompts/responses.ts
+++ b/src/core/prompts/responses.ts
@@ -6,12 +6,6 @@ import { ClineIgnoreController, LOCK_TEXT_SYMBOL } from "../ignore/ClineIgnoreCo
 export const formatResponse = {
 	toolDenied: () => `The user denied this operation.`,
 
-	toolDeniedWithFeedback: (feedback?: string) =>
-		`The user denied this operation and provided the following feedback:\n<feedback>\n${feedback}\n</feedback>`,
-
-	toolApprovedWithFeedback: (feedback?: string) =>
-		`The user approved this operation and provided the following feedback:\n<feedback>\n${feedback}\n</feedback>`,
-
 	toolError: (error?: string) => `The tool execution failed with the following error:\n<error>\n${error}\n</error>`,
 
 	clineIgnoreError: (path: string) =>