diff --git a/src/core/Cline.ts b/src/core/Cline.ts
index 7d40127edf..faa04cf110 100644
--- a/src/core/Cline.ts
+++ b/src/core/Cline.ts
@@ -1542,7 +1542,9 @@ export class Cline {
 				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.userMessageContent.push({
@@ -1560,15 +1562,24 @@ export class Cline {
 							this.didRejectTool = true
 							return false
 						}
+						// Rejection WITHOUT explicit feedback
 						pushToolResult(formatResponse.toolDenied())
 						// this.toolResults.push({
 						// 	type: "tool_result",
 						// 	tool_use_id: toolUseId,
 						// 	content: await this.formatToolDenied(),
 						// })
-						this.didRejectTool = true
+						this.didRejectTool = true // Prevent further tool uses in this message
 						return false
 					}
+
+					// 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
 				}
 
diff --git a/src/core/prompts/responses.ts b/src/core/prompts/responses.ts
index 623e3d8806..8a14acc02b 100644
--- a/src/core/prompts/responses.ts
+++ b/src/core/prompts/responses.ts
@@ -9,6 +9,9 @@ export const formatResponse = {
 	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) =>
diff --git a/webview-ui/src/components/chat/ChatView.tsx b/webview-ui/src/components/chat/ChatView.tsx
index cad6e84aff..8b4290cd2a 100644
--- a/webview-ui/src/components/chat/ChatView.tsx
+++ b/webview-ui/src/components/chat/ChatView.tsx
@@ -324,67 +324,99 @@ const ChatView = ({ isHidden, showAnnouncement, hideAnnouncement, showHistoryVie
 	/*
 	This logic depends on the useEffect[messages] above to set clineAsk, after which buttons are shown and we then send an askResponse to the extension.
 	*/
-	const handlePrimaryButtonClick = useCallback(() => {
-		switch (clineAsk) {
-			case "api_req_failed":
-			case "command":
-			case "command_output":
-			case "tool":
-			case "browser_action_launch":
-			case "use_mcp_server":
-			case "resume_task":
-			case "mistake_limit_reached":
-			case "auto_approval_max_req_reached":
-				vscode.postMessage({
-					type: "askResponse",
-					askResponse: "yesButtonClicked",
-				})
-				break
-			case "completion_result":
-			case "resume_completed_task":
-				// extension waiting for feedback. but we can just present a new task button
-				startNewTask()
-				break
-		}
-		setTextAreaDisabled(true)
-		setClineAsk(undefined)
-		setEnableButtons(false)
-		// setPrimaryButtonText(undefined)
-		// setSecondaryButtonText(undefined)
-		disableAutoScrollRef.current = false
-	}, [clineAsk, startNewTask])
+	const handlePrimaryButtonClick = useCallback(
+		(text?: string, images?: string[]) => {
+			const trimmedInput = text?.trim()
+			switch (clineAsk) {
+				case "api_req_failed":
+				case "command":
+				case "command_output":
+				case "tool":
+				case "browser_action_launch":
+				case "use_mcp_server":
+				case "resume_task":
+				case "mistake_limit_reached":
+				case "auto_approval_max_req_reached":
+					if (trimmedInput || (images && images.length > 0)) {
+						vscode.postMessage({
+							type: "askResponse",
+							askResponse: "yesButtonClicked",
+							text: trimmedInput,
+							images: images,
+						})
+					} else {
+						vscode.postMessage({
+							type: "askResponse",
+							askResponse: "yesButtonClicked",
+						})
+					}
+					// Clear input state after sending
+					setInputValue("")
+					setSelectedImages([])
+					break
+				case "completion_result":
+				case "resume_completed_task":
+					// extension waiting for feedback. but we can just present a new task button
+					startNewTask()
+					break
+			}
+			setTextAreaDisabled(true)
+			setClineAsk(undefined)
+			setEnableButtons(false)
+			// setPrimaryButtonText(undefined)
+			// setSecondaryButtonText(undefined)
+			disableAutoScrollRef.current = false
+		},
+		[clineAsk, startNewTask],
+	)
 
-	const handleSecondaryButtonClick = useCallback(() => {
-		if (isStreaming) {
-			vscode.postMessage({ type: "cancelTask" })
-			setDidClickCancel(true)
-			return
-		}
+	const handleSecondaryButtonClick = useCallback(
+		(text?: string, images?: string[]) => {
+			const trimmedInput = text?.trim()
+			if (isStreaming) {
+				vscode.postMessage({ type: "cancelTask" })
+				setDidClickCancel(true)
+				return
+			}
 
-		switch (clineAsk) {
-			case "api_req_failed":
-			case "mistake_limit_reached":
-			case "auto_approval_max_req_reached":
-				startNewTask()
-				break
-			case "command":
-			case "tool":
-			case "browser_action_launch":
-			case "use_mcp_server":
-				// responds to the API with a "This operation failed" and lets it try again
-				vscode.postMessage({
-					type: "askResponse",
-					askResponse: "noButtonClicked",
-				})
-				break
-		}
-		setTextAreaDisabled(true)
-		setClineAsk(undefined)
-		setEnableButtons(false)
-		// setPrimaryButtonText(undefined)
-		// setSecondaryButtonText(undefined)
-		disableAutoScrollRef.current = false
-	}, [clineAsk, startNewTask, isStreaming])
+			switch (clineAsk) {
+				case "api_req_failed":
+				case "mistake_limit_reached":
+				case "auto_approval_max_req_reached":
+					startNewTask()
+					break
+				case "command":
+				case "tool":
+				case "browser_action_launch":
+				case "use_mcp_server":
+					if (trimmedInput || (images && images.length > 0)) {
+						vscode.postMessage({
+							type: "askResponse",
+							askResponse: "noButtonClicked",
+							text: trimmedInput,
+							images: images,
+						})
+					} else {
+						// responds to the API with a "This operation failed" and lets it try again
+						vscode.postMessage({
+							type: "askResponse",
+							askResponse: "noButtonClicked",
+						})
+					}
+					// Clear input state after sending
+					setInputValue("")
+					setSelectedImages([])
+					break
+			}
+			setTextAreaDisabled(true)
+			setClineAsk(undefined)
+			setEnableButtons(false)
+			// setPrimaryButtonText(undefined)
+			// setSecondaryButtonText(undefined)
+			disableAutoScrollRef.current = false
+		},
+		[clineAsk, startNewTask, isStreaming],
+	)
 
 	const handleTaskCloseButtonClick = useCallback(() => {
 		startNewTask()
@@ -426,10 +458,10 @@ const ChatView = ({ isHidden, showAnnouncement, hideAnnouncement, showHistoryVie
 							handleSendMessage(message.text ?? "", message.images ?? [])
 							break
 						case "primaryButtonClick":
-							handlePrimaryButtonClick()
+							handlePrimaryButtonClick(message.text ?? "", message.images ?? [])
 							break
 						case "secondaryButtonClick":
-							handleSecondaryButtonClick()
+							handleSecondaryButtonClick(message.text ?? "", message.images ?? [])
 							break
 					}
 			}
@@ -869,7 +901,7 @@ const ChatView = ({ isHidden, showAnnouncement, hideAnnouncement, showHistoryVie
 										flex: secondaryButtonText ? 1 : 2,
 										marginRight: secondaryButtonText ? "6px" : "0",
 									}}
-									onClick={handlePrimaryButtonClick}>
+									onClick={() => handlePrimaryButtonClick(inputValue, selectedImages)}>
 									{primaryButtonText}
 								</VSCodeButton>
 							)}
@@ -881,7 +913,7 @@ const ChatView = ({ isHidden, showAnnouncement, hideAnnouncement, showHistoryVie
 										flex: isStreaming ? 2 : 1,
 										marginLeft: isStreaming ? 0 : "6px",
 									}}
-									onClick={handleSecondaryButtonClick}>
+									onClick={() => handleSecondaryButtonClick(inputValue, selectedImages)}>
 									{isStreaming ? "Cancel" : secondaryButtonText}
 								</VSCodeButton>
 							)}