diff --git a/.gitignore b/.gitignore
index 0c032bbf76..e45916d7e7 100644
--- a/.gitignore
+++ b/.gitignore
@@ -6,6 +6,10 @@ node_modules
 coverage/
 mock/
 
+# Webview UI specific ignores
+webview-ui/node_modules
+webview-ui/dist
+
 .DS_Store
 
 # IDEs
diff --git a/webview-ui/src/components/chat/AutoApproveMenu.tsx b/webview-ui/src/components/chat/AutoApproveMenu.tsx
index ac02d6b8c4..e7f59f606c 100644
--- a/webview-ui/src/components/chat/AutoApproveMenu.tsx
+++ b/webview-ui/src/components/chat/AutoApproveMenu.tsx
@@ -43,6 +43,7 @@ const AutoApproveMenu = ({ style }: AutoApproveMenuProps) => {
 		(key: AutoApproveSetting, value: boolean) => {
 			vscode.postMessage({ type: key, bool: value })
 
+			// Update the specific setting
 			switch (key) {
 				case "alwaysAllowReadOnly":
 					setAlwaysAllowReadOnly(value)
@@ -69,6 +70,29 @@ const AutoApproveMenu = ({ style }: AutoApproveMenuProps) => {
 					setAlwaysApproveResubmit(value)
 					break
 			}
+
+			// After updating the specific setting, check if any action is now enabled.
+			// If so, ensure autoApprovalEnabled is true.
+			// This needs to be done after the state updates, so we'll use a temporary check
+			// or re-evaluate the `toggles` object.
+			// For simplicity, we'll assume the `toggles` state will reflect the change
+			// in the next render cycle, and we can force autoApprovalEnabled to true
+			// if any action is being enabled.
+			if (value === true) {
+				setAutoApprovalEnabled(true)
+				vscode.postMessage({ type: "autoApprovalEnabled", bool: true })
+			} else {
+				// If an action is being disabled, check if all are now disabled.
+				// If so, set autoApprovalEnabled to false.
+				// This requires re-evaluating the state of all toggles *after* the current one is set.
+				// A more robust solution would involve passing the updated `toggles` object
+				// or re-calculating `hasAnyAutoApprovedAction` here.
+				// For now, let's rely on the `hasAnyAutoApprovedAction` memoized value
+				// which will update on the next render.
+				// If the user unchecks the last enabled option, autoApprovalEnabled should become false.
+				// This logic is already handled by the main checkbox's disabled state in the collapsed view.
+				// So, we only need to ensure it turns ON when an individual is turned ON.
+			}
 		},
 		[
 			setAlwaysAllowReadOnly,
@@ -79,6 +103,7 @@ const AutoApproveMenu = ({ style }: AutoApproveMenuProps) => {
 			setAlwaysAllowModeSwitch,
 			setAlwaysAllowSubtasks,
 			setAlwaysApproveResubmit,
+			setAutoApprovalEnabled, // Added setAutoApprovalEnabled to dependencies
 		],
 	)
 
@@ -107,10 +132,17 @@ const AutoApproveMenu = ({ style }: AutoApproveMenuProps) => {
 		],
 	)
 
-	const enabledActionsList = Object.entries(toggles)
-		.filter(([_key, value]) => !!value)
-		.map(([key]) => t(autoApproveSettingsConfig[key as AutoApproveSetting].labelKey))
-		.join(", ")
+	const hasAnyAutoApprovedAction = useMemo(() => Object.values(toggles).some((value) => !!value), [toggles])
+
+	const displayedAutoApproveText = useMemo(() => {
+		if (autoApprovalEnabled && hasAnyAutoApprovedAction) {
+			return Object.entries(toggles)
+				.filter(([_key, value]) => !!value)
+				.map(([key]) => t(autoApproveSettingsConfig[key as AutoApproveSetting].labelKey))
+				.join(", ")
+		}
+		return t("chat:autoApprove.none")
+	}, [autoApprovalEnabled, hasAnyAutoApprovedAction, toggles, t])
 
 	const handleOpenSettings = useCallback(
 		() =>
@@ -140,9 +172,10 @@ const AutoApproveMenu = ({ style }: AutoApproveMenuProps) => {
 				onClick={toggleExpanded}>
 				<div onClick={(e) => e.stopPropagation()}>
 					<VSCodeCheckbox
-						checked={autoApprovalEnabled ?? false}
+						checked={autoApprovalEnabled && hasAnyAutoApprovedAction}
+						disabled={!hasAnyAutoApprovedAction}
 						onChange={() => {
-							const newValue = !(autoApprovalEnabled ?? false)
+							const newValue = !(autoApprovalEnabled && hasAnyAutoApprovedAction)
 							setAutoApprovalEnabled(newValue)
 							vscode.postMessage({ type: "autoApprovalEnabled", bool: newValue })
 						}}
@@ -172,7 +205,7 @@ const AutoApproveMenu = ({ style }: AutoApproveMenuProps) => {
 							flex: 1,
 							minWidth: 0,
 						}}>
-						{enabledActionsList || t("chat:autoApprove.none")}
+						{displayedAutoApproveText}
 					</span>
 					<span
 						className={`codicon codicon-chevron-${isExpanded ? "down" : "right"}`}
@@ -199,7 +232,11 @@ const AutoApproveMenu = ({ style }: AutoApproveMenuProps) => {
 						/>
 					</div>
 
-					<AutoApproveToggle {...toggles} onToggle={onAutoApproveToggle} />
+					<AutoApproveToggle
+						{...toggles}
+						onToggle={onAutoApproveToggle}
+						isOverallApprovalEnabled={autoApprovalEnabled}
+					/>
 
 					{/* Auto-approve API request count limit input row inspired by Cline */}
 					<div
diff --git a/webview-ui/src/components/settings/AutoApproveToggle.tsx b/webview-ui/src/components/settings/AutoApproveToggle.tsx
index ffad47e2ac..9b20a301f3 100644
--- a/webview-ui/src/components/settings/AutoApproveToggle.tsx
+++ b/webview-ui/src/components/settings/AutoApproveToggle.tsx
@@ -87,9 +87,10 @@ export const autoApproveSettingsConfig: Record<AutoApproveSetting, AutoApproveCo
 
 type AutoApproveToggleProps = AutoApproveToggles & {
 	onToggle: (key: AutoApproveSetting, value: boolean) => void
+	isOverallApprovalEnabled?: boolean // New prop
 }
 
-export const AutoApproveToggle = ({ onToggle, ...props }: AutoApproveToggleProps) => {
+export const AutoApproveToggle = ({ onToggle, isOverallApprovalEnabled, ...props }: AutoApproveToggleProps) => {
 	const { t } = useAppTranslation()
 
 	return (
@@ -99,22 +100,28 @@ export const AutoApproveToggle = ({ onToggle, ...props }: AutoApproveToggleProps
 				"[@media(min-width:600px)]:gap-4",
 				"[@media(min-width:800px)]:max-w-[800px]",
 			)}>
-			{Object.values(autoApproveSettingsConfig).map(({ key, descriptionKey, labelKey, icon, testId }) => (
-				<Button
-					key={key}
-					variant={props[key] ? "default" : "outline"}
-					onClick={() => onToggle(key, !props[key])}
-					title={t(descriptionKey || "")}
-					aria-label={t(labelKey)}
-					aria-pressed={!!props[key]}
-					data-testid={testId}
-					className={cn(" aspect-square h-[80px]", !props[key] && "opacity-50")}>
-					<span className={cn("flex flex-col items-center gap-1")}>
-						<span className={`codicon codicon-${icon}`} />
-						<span className="text-sm text-center">{t(labelKey)}</span>
-					</span>
-				</Button>
-			))}
+			{Object.values(autoApproveSettingsConfig).map(({ key, descriptionKey, labelKey, icon, testId }) => {
+				const isButtonActive = props[key] // This reflects the actual state of the individual toggle
+				const isButtonVisuallyEnabled = isOverallApprovalEnabled === false ? false : isButtonActive
+
+				return (
+					<Button
+						key={key}
+						variant={isButtonActive ? "default" : "outline"} // Variant always reflects its own state
+						onClick={() => onToggle(key, !props[key])}
+						title={t(descriptionKey || "")}
+						aria-label={t(labelKey)}
+						aria-pressed={!!isButtonActive}
+						data-testid={testId}
+						className={cn(" aspect-square h-[80px]", !isButtonVisuallyEnabled && "opacity-50")} // Opacity based on overall state
+					>
+						<span className={cn("flex flex-col items-center gap-1")}>
+							<span className={`codicon codicon-${icon}`} />
+							<span className="text-sm text-center">{t(labelKey)}</span>
+						</span>
+					</Button>
+				)
+			})}
 		</div>
 	)
 }