diff --git a/src/core/Cline.ts b/src/core/Cline.ts
index 127960f073..e088f0073b 100644
--- a/src/core/Cline.ts
+++ b/src/core/Cline.ts
@@ -2707,14 +2707,15 @@ export class Cline {
 								this.isAwaitingPlanResponse = false
 
 								if (this.didRespondToPlanAskBySwitchingMode) {
-									// await this.say("user_feedback", text ?? "", images)
 									pushToolResult(
 										formatResponse.toolResult(
 											`[The user has switched to ACT MODE, so you may now proceed with the task.]`,
 											images,
 										),
 									)
-								} else {
+								}
+
+								if (text) {
 									await this.say("user_feedback", text ?? "", images)
 									pushToolResult(formatResponse.toolResult(`<user_message>\n${text}\n</user_message>`, images))
 								}
diff --git a/src/core/webview/ClineProvider.ts b/src/core/webview/ClineProvider.ts
index 397e11eb80..6fb3f415ab 100644
--- a/src/core/webview/ClineProvider.ts
+++ b/src/core/webview/ClineProvider.ts
@@ -618,7 +618,8 @@ export class ClineProvider implements vscode.WebviewViewProvider {
 									await this.postMessageToWebview({
 										type: "invoke",
 										invoke: "sendMessage",
-										text: "[Proceeding with the task...]",
+										text: message.chatContent?.message || "[Proceeding with the task...]",
+										images: message.chatContent?.images,
 									})
 								} else {
 									this.cancelTask()
diff --git a/src/shared/ChatContent.ts b/src/shared/ChatContent.ts
new file mode 100644
index 0000000000..fe209de363
--- /dev/null
+++ b/src/shared/ChatContent.ts
@@ -0,0 +1,4 @@
+export interface ChatContent {
+	message?: string
+	images?: string[]
+}
diff --git a/src/shared/WebviewMessage.ts b/src/shared/WebviewMessage.ts
index a18a3c405a..447193dd18 100644
--- a/src/shared/WebviewMessage.ts
+++ b/src/shared/WebviewMessage.ts
@@ -2,6 +2,7 @@ import { ApiConfiguration } from "./api"
 import { AutoApprovalSettings } from "./AutoApprovalSettings"
 import { BrowserSettings } from "./BrowserSettings"
 import { ChatSettings } from "./ChatSettings"
+import { ChatContent } from "./ChatContent"
 
 export interface WebviewMessage {
 	type:
@@ -53,6 +54,7 @@ export interface WebviewMessage {
 	autoApprovalSettings?: AutoApprovalSettings
 	browserSettings?: BrowserSettings
 	chatSettings?: ChatSettings
+	chatContent?: ChatContent
 
 	// For toggleToolAutoApprove
 	serverName?: string
diff --git a/src/test/webview/chat-native.test.ts b/src/test/webview/chat-native.test.ts
index 775af4b7ae..d3fe630a94 100644
--- a/src/test/webview/chat-native.test.ts
+++ b/src/test/webview/chat-native.test.ts
@@ -28,7 +28,13 @@ describe("Chat Integration Tests", () => {
                                     vscode.postMessage({ type: 'newTask', text: message.text });
                                     break;
                                 case 'toggleMode':
-                                    vscode.postMessage({ type: 'chatSettings', chatSettings: { mode: 'act' } });
+                                    vscode.postMessage({
+                                        type: 'chatSettings',
+                                        chatSettings: { mode: 'act' }, 
+                                        chatContent: {
+                                            message: "message test",
+                                        }
+                                    });
                                     break;
                                 case 'invoke':
                                     if (message.invoke === 'primaryButtonClick') {
@@ -92,6 +98,25 @@ describe("Chat Integration Tests", () => {
 		assert.equal(stateChange.chatSettings.mode, "act")
 	})
 
+	it("should toggle between plan and act modes with messages", async () => {
+		// Set up state change listener
+		const stateChangePromise = new Promise<any>((resolve) => {
+			panel.webview.onDidReceiveMessage((message) => {
+				if (message.type === "chatSettings") {
+					resolve(message)
+				}
+			})
+		})
+
+		// Trigger mode toggle
+		await panel.webview.postMessage({ type: "toggleMode" })
+
+		// Verify mode changed
+		const stateChange = await stateChangePromise
+		assert.equal(stateChange.chatSettings.mode, "act")
+		assert.equal(stateChange.chatContent.message, "message test")
+	})
+
 	it("should handle tool approval flow", async () => {
 		// Set up approval listener
 		const approvalPromise = new Promise<any>((resolve) => {
diff --git a/webview-ui/src/components/chat/ChatTextArea.tsx b/webview-ui/src/components/chat/ChatTextArea.tsx
index 0255ef0301..e86697405f 100644
--- a/webview-ui/src/components/chat/ChatTextArea.tsx
+++ b/webview-ui/src/components/chat/ChatTextArea.tsx
@@ -616,13 +616,17 @@ const ChatTextArea = forwardRef<HTMLTextAreaElement, ChatTextAreaProps>(
 					chatSettings: {
 						mode: newMode,
 					},
+					chatContent: {
+						message: inputValue.trim() ? inputValue : undefined,
+						images: selectedImages.length > 0 ? selectedImages : undefined,
+					},
 				})
 				// Focus the textarea after mode toggle with slight delay
 				setTimeout(() => {
 					textAreaRef.current?.focus()
 				}, 100)
 			}, changeModeDelay)
-		}, [chatSettings.mode, showModelSelector, submitApiConfig])
+		}, [chatSettings.mode, showModelSelector, submitApiConfig, inputValue, selectedImages])
 
 		useShortcut("Meta+Shift+a", onModeToggle, { disableTextInputs: false }) // important that we don't disable the text input here