feat: add "Always run enhance prompt" setting for automatic prompt enhancement

- Added alwaysRunEnhancePrompt boolean setting to global settings schema
- Added toggle control in PromptsSettings component under "Enhance prompt"
- Updated ExtensionStateContext to handle the new setting with getter/setter
- Modified ChatTextArea to auto-enhance prompts when setting is enabled
- Auto-enhancement triggers on Enter keypress for new tasks only
- Enhanced text is automatically sent after processing
- All existing tests passing with proper null checks for clineMessages

Fixes #9649

packages/types/src/global-settings.ts

@@ -184,6 +184,7 @@ export const globalSettingsSchema = z.object({
 	customModePrompts: customModePromptsSchema.optional(),
 	customSupportPrompts: customSupportPromptsSchema.optional(),
 	enhancementApiConfigId: z.string().optional(),
+	alwaysRunEnhancePrompt: z.boolean().optional(),
 	includeTaskHistoryInEnhance: z.boolean().optional(),
 	historyPreviewCollapsed: z.boolean().optional(),
 	reasoningBlockCollapsed: z.boolean().optional(),

src/shared/ExtensionMessage.ts

@@ -276,6 +276,7 @@ export type ExtensionState = Pick<
 	| "customModePrompts"
 	| "customSupportPrompts"
 	| "enhancementApiConfigId"
+	| "alwaysRunEnhancePrompt"
 	| "condensingApiConfigId"
 	| "customCondensingPrompt"
 	| "codebaseIndexConfig"

webview-ui/src/components/chat/ChatTextArea.tsx

@@ -94,6 +94,7 @@ export const ChatTextArea = forwardRef<HTMLTextAreaElement, ChatTextAreaProps>(
 			clineMessages,
 			commands,
 			cloudUserInfo,
+			alwaysRunEnhancePrompt,
 		} = useExtensionState()
 
 		// Find the ID and display text for the currently selected API configuration.
@@ -123,6 +124,8 @@ export const ChatTextArea = forwardRef<HTMLTextAreaElement, ChatTextAreaProps>(
 			return () => document.removeEventListener("mousedown", handleClickOutside)
 		}, [showDropdown])
 
+		const [pendingSend, setPendingSend] = useState(false)
+
 		// Handle enhanced prompt response and search results.
 		useEffect(() => {
 			const messageHandler = (event: MessageEvent) => {
@@ -151,6 +154,12 @@ export const ChatTextArea = forwardRef<HTMLTextAreaElement, ChatTextAreaProps>(
 					}
 
 					setIsEnhancingPrompt(false)
+
+					// If we were waiting to send after enhancement, send now
+					if (pendingSend) {
+						setPendingSend(false)
+						onSend()
+					}
 				} else if (message.type === "insertTextIntoTextarea") {
 					if (message.text && textAreaRef.current) {
 						// Insert the command text at the current cursor position
@@ -201,7 +210,7 @@ export const ChatTextArea = forwardRef<HTMLTextAreaElement, ChatTextAreaProps>(
 
 			window.addEventListener("message", messageHandler)
 			return () => window.removeEventListener("message", messageHandler)
-		}, [setInputValue, searchRequestId, inputValue])
+		}, [setInputValue, searchRequestId, inputValue, pendingSend, onSend])
 
 		const [isDraggingOver, setIsDraggingOver] = useState(false)
 		const [textAreaBaseHeight, setTextAreaBaseHeight] = useState<number | undefined>(undefined)
@@ -474,10 +483,19 @@ export const ChatTextArea = forwardRef<HTMLTextAreaElement, ChatTextAreaProps>(
 
 				if (event.key === "Enter" && !event.shiftKey && !isComposing) {
 					event.preventDefault()
-
-					// Always call onSend - let ChatView handle queueing when disabled
 					resetHistoryNavigation()
-					onSend()
+
+					// Check if we should auto-enhance first
+					const trimmedInput = inputValue.trim()
+					if (alwaysRunEnhancePrompt && trimmedInput && clineMessages?.length === 0) {
+						// This is a new task and auto-enhance is enabled
+						setIsEnhancingPrompt(true)
+						setPendingSend(true)
+						vscode.postMessage({ type: "enhancePrompt" as const, text: trimmedInput })
+					} else {
+						// Normal send without enhancement
+						onSend()
+					}
 				}
 
 				if (event.key === "Backspace" && !isComposing) {
@@ -541,6 +559,8 @@ export const ChatTextArea = forwardRef<HTMLTextAreaElement, ChatTextAreaProps>(
 				handleHistoryNavigation,
 				resetHistoryNavigation,
 				commands,
+				alwaysRunEnhancePrompt,
+				clineMessages?.length,
 			],
 		)
 

webview-ui/src/components/settings/PromptsSettings.tsx

@@ -38,6 +38,8 @@ const PromptsSettings = ({
 		listApiConfigMeta,
 		enhancementApiConfigId,
 		setEnhancementApiConfigId,
+		alwaysRunEnhancePrompt,
+		setAlwaysRunEnhancePrompt,
 		condensingApiConfigId,
 		setCondensingApiConfigId,
 		customCondensingPrompt,
@@ -283,6 +285,33 @@ const PromptsSettings = ({
 										</div>
 									</div>
 
+									<div>
+										<VSCodeCheckbox
+											checked={alwaysRunEnhancePrompt}
+											onChange={(e: Event | FormEvent<HTMLElement>) => {
+												const target = (
+													"target" in e ? e.target : null
+												) as HTMLInputElement | null
+
+												if (!target) {
+													return
+												}
+
+												setAlwaysRunEnhancePrompt(target.checked)
+
+												vscode.postMessage({
+													type: "updateSettings",
+													updatedSettings: { alwaysRunEnhancePrompt: target.checked },
+												})
+											}}>
+											<span className="font-medium">Always run enhance prompt</span>
+										</VSCodeCheckbox>
+										<div className="text-vscode-descriptionForeground text-sm mt-1 mb-3">
+											Automatically enhance every message before sending it to improve quality and
+											clarity
+										</div>
+									</div>
+
 									<div>
 										<label className="block font-medium mb-1">
 											{t("prompts:supportPrompts.enhance.testEnhancement")}

webview-ui/src/context/ExtensionStateContext.tsx

@@ -122,6 +122,8 @@ export interface ExtensionStateContextType extends ExtensionState {
 	setCustomSupportPrompts: (value: CustomSupportPrompts) => void
 	enhancementApiConfigId?: string
 	setEnhancementApiConfigId: (value: string) => void
+	alwaysRunEnhancePrompt?: boolean
+	setAlwaysRunEnhancePrompt: (value: boolean) => void
 	setExperimentEnabled: (id: ExperimentId, enabled: boolean) => void
 	setAutoApprovalEnabled: (value: boolean) => void
 	customModes: ModeConfig[]
@@ -228,6 +230,7 @@ export const ExtensionStateContextProvider: React.FC<{ children: React.ReactNode
 		customSupportPrompts: {},
 		experiments: experimentDefault,
 		enhancementApiConfigId: "",
+		alwaysRunEnhancePrompt: false, // Default to false for backward compatibility
 		condensingApiConfigId: "", // Default empty string for condensing API config ID
 		customCondensingPrompt: "", // Default empty string for custom condensing prompt
 		hasOpenedModeSelector: false, // Default to false (not opened yet)
@@ -295,6 +298,7 @@ export const ExtensionStateContextProvider: React.FC<{ children: React.ReactNode
 		project: {},
 		global: {},
 	})
+	const [alwaysRunEnhancePrompt, setAlwaysRunEnhancePrompt] = useState(false)
 	const [includeTaskHistoryInEnhance, setIncludeTaskHistoryInEnhance] = useState(true)
 	const [prevCloudIsAuthenticated, setPrevCloudIsAuthenticated] = useState(false)
 	const [includeCurrentTime, setIncludeCurrentTime] = useState(true)
@@ -332,6 +336,10 @@ export const ExtensionStateContextProvider: React.FC<{ children: React.ReactNode
 					if ((newState as any).followupAutoApproveTimeoutMs !== undefined) {
 						setFollowupAutoApproveTimeoutMs((newState as any).followupAutoApproveTimeoutMs)
 					}
+					// Update alwaysRunEnhancePrompt if present in state message
+					if ((newState as any).alwaysRunEnhancePrompt !== undefined) {
+						setAlwaysRunEnhancePrompt((newState as any).alwaysRunEnhancePrompt)
+					}
 					// Update includeTaskHistoryInEnhance if present in state message
 					if ((newState as any).includeTaskHistoryInEnhance !== undefined) {
 						setIncludeTaskHistoryInEnhance((newState as any).includeTaskHistoryInEnhance)
@@ -474,6 +482,7 @@ export const ExtensionStateContextProvider: React.FC<{ children: React.ReactNode
 		profileThresholds: state.profileThresholds ?? {},
 		alwaysAllowFollowupQuestions,
 		followupAutoApproveTimeoutMs,
+		alwaysRunEnhancePrompt,
 		remoteControlEnabled: state.remoteControlEnabled ?? false,
 		taskSyncEnabled: state.taskSyncEnabled,
 		featureRoomoteControlEnabled: state.featureRoomoteControlEnabled ?? false,
@@ -493,6 +502,7 @@ export const ExtensionStateContextProvider: React.FC<{ children: React.ReactNode
 		setAlwaysAllowModeSwitch: (value) => setState((prevState) => ({ ...prevState, alwaysAllowModeSwitch: value })),
 		setAlwaysAllowSubtasks: (value) => setState((prevState) => ({ ...prevState, alwaysAllowSubtasks: value })),
 		setAlwaysAllowFollowupQuestions,
+		setAlwaysRunEnhancePrompt,
 		setFollowupAutoApproveTimeoutMs: (value) =>
 			setState((prevState) => ({ ...prevState, followupAutoApproveTimeoutMs: value })),
 		setShowAnnouncement: (value) => setState((prevState) => ({ ...prevState, shouldShowAnnouncement: value })),