diff --git a/packages/types/src/vscode.ts b/packages/types/src/vscode.ts
index 00f6bbbcba9..cddac614306 100644
--- a/packages/types/src/vscode.ts
+++ b/packages/types/src/vscode.ts
@@ -53,6 +53,7 @@ export const commandIds = [
 	"focusInput",
 	"acceptInput",
 	"focusPanel",
+	"enhancePrompt",
 ] as const
 
 export type CommandId = (typeof commandIds)[number]
diff --git a/src/activate/registerCommands.ts b/src/activate/registerCommands.ts
index bd925b0e900..fbd4db3e904 100644
--- a/src/activate/registerCommands.ts
+++ b/src/activate/registerCommands.ts
@@ -218,6 +218,15 @@ const getCommandsMap = ({ context, outputChannel, provider }: RegisterCommandOpt
 
 		visibleProvider.postMessageToWebview({ type: "acceptInput" })
 	},
+	enhancePrompt: () => {
+		const visibleProvider = getVisibleProviderOrLog(outputChannel)
+
+		if (!visibleProvider) {
+			return
+		}
+
+		visibleProvider.postMessageToWebview({ type: "action", action: "triggerEnhancePrompt" as any })
+	},
 })
 
 export const openClineInNewTab = async ({ context, outputChannel }: Omit<RegisterCommandOptions, "provider">) => {
diff --git a/src/package.json b/src/package.json
index 5e3cd3bc530..8474e6b2f74 100644
--- a/src/package.json
+++ b/src/package.json
@@ -174,6 +174,11 @@
 				"command": "roo-cline.acceptInput",
 				"title": "%command.acceptInput.title%",
 				"category": "%configuration.title%"
+			},
+			{
+				"command": "roo-cline.enhancePrompt",
+				"title": "%command.enhancePrompt.title%",
+				"category": "%configuration.title%"
 			}
 		],
 		"menus": {
@@ -388,7 +393,15 @@
 					"description": "%settings.autoImportSettingsPath.description%"
 				}
 			}
-		}
+		},
+		"keybindings": [
+			{
+				"command": "roo-cline.enhancePrompt",
+				"key": "ctrl+shift+e",
+				"mac": "cmd+shift+e",
+				"when": "view == roo-cline.SidebarProvider || activeWebviewPanelId == roo-cline.TabPanelProvider"
+			}
+		]
 	},
 	"scripts": {
 		"lint": "eslint . --ext=ts --max-warnings=0",
diff --git a/src/shared/ExtensionMessage.ts b/src/shared/ExtensionMessage.ts
index 4f2aa2da159..ea641f87045 100644
--- a/src/shared/ExtensionMessage.ts
+++ b/src/shared/ExtensionMessage.ts
@@ -120,6 +120,7 @@ export interface ExtensionMessage {
 		| "didBecomeVisible"
 		| "focusInput"
 		| "switchTab"
+		| "triggerEnhancePrompt"
 	invoke?: "newChat" | "sendMessage" | "primaryButtonClick" | "secondaryButtonClick" | "setChatBoxMessage"
 	state?: ExtensionState
 	images?: string[]
diff --git a/src/shared/WebviewMessage.ts b/src/shared/WebviewMessage.ts
index 1f56829f7b3..d35a1b58ddd 100644
--- a/src/shared/WebviewMessage.ts
+++ b/src/shared/WebviewMessage.ts
@@ -110,6 +110,7 @@ export interface WebviewMessage {
 		| "diagnosticsEnabled"
 		| "enhancePrompt"
 		| "enhancedPrompt"
+		| "triggerEnhancePrompt"
 		| "draggedImages"
 		| "deleteMessage"
 		| "deleteMessageConfirm"
diff --git a/webview-ui/src/App.tsx b/webview-ui/src/App.tsx
index 3c4c14f5dfe..abe3cfa6a00 100644
--- a/webview-ui/src/App.tsx
+++ b/webview-ui/src/App.tsx
@@ -169,6 +169,10 @@ const App = () => {
 			if (message.type === "acceptInput") {
 				chatViewRef.current?.acceptInput()
 			}
+
+			if (message.type === "action" && message.action === "triggerEnhancePrompt") {
+				chatViewRef.current?.triggerEnhancePrompt()
+			}
 		},
 		[switchTab],
 	)
diff --git a/webview-ui/src/components/chat/ChatTextArea.tsx b/webview-ui/src/components/chat/ChatTextArea.tsx
index 6c541353eb2..afb394f2995 100644
--- a/webview-ui/src/components/chat/ChatTextArea.tsx
+++ b/webview-ui/src/components/chat/ChatTextArea.tsx
@@ -31,6 +31,8 @@ import { cn } from "@/lib/utils"
 import { usePromptHistory } from "./hooks/usePromptHistory"
 import { EditModeControls } from "./EditModeControls"
 
+const isMac = navigator.platform.toUpperCase().indexOf("MAC") >= 0
+
 interface ChatTextAreaProps {
 	inputValue: string
 	setInputValue: (value: string) => void
@@ -1110,7 +1112,7 @@ const ChatTextArea = forwardRef<HTMLTextAreaElement, ChatTextAreaProps>(
 				/>
 
 				<div className="absolute top-1 right-1 z-30">
-					<StandardTooltip content={t("chat:enhancePrompt")}>
+					<StandardTooltip content={`${t("chat:enhancePrompt")} (${isMac ? "⌘" : "Ctrl"}+Shift+E)`}>
 						<button
 							aria-label={t("chat:enhancePrompt")}
 							disabled={sendingDisabled}
diff --git a/webview-ui/src/components/chat/ChatView.tsx b/webview-ui/src/components/chat/ChatView.tsx
index f804f7b61ed..de370f9a884 100644
--- a/webview-ui/src/components/chat/ChatView.tsx
+++ b/webview-ui/src/components/chat/ChatView.tsx
@@ -65,6 +65,7 @@ export interface ChatViewProps {
 
 export interface ChatViewRef {
 	acceptInput: () => void
+	triggerEnhancePrompt: () => void
 }
 
 export const MAX_IMAGES_PER_MESSAGE = 20 // Anthropic limits to 20 images
@@ -1616,6 +1617,13 @@ const ChatViewComponent: React.ForwardRefRenderFunction<ChatViewRef, ChatViewPro
 				handleSendMessage(inputValue, selectedImages)
 			}
 		},
+		triggerEnhancePrompt: () => {
+			// Find the enhance prompt button and trigger its click
+			const enhanceButton = document.querySelector('[aria-label*="enhance"]') as HTMLButtonElement
+			if (enhanceButton && !sendingDisabled) {
+				enhanceButton.click()
+			}
+		},
 	}))
 
 	const handleCondenseContext = (taskId: string) => {