diff --git a/webview-ui/src/components/chat/AutoApproveMenu.tsx b/webview-ui/src/components/chat/AutoApproveMenu.tsx
index 8961fc7f5d..b76601ea9e 100644
--- a/webview-ui/src/components/chat/AutoApproveMenu.tsx
+++ b/webview-ui/src/components/chat/AutoApproveMenu.tsx
@@ -1,14 +1,18 @@
 import { memo, useCallback, useMemo, useState } from "react"
 import { Trans } from "react-i18next"
 import { VSCodeCheckbox, VSCodeLink } from "@vscode/webview-ui-toolkit/react"
+import { Stamp, ListChecks, LayoutList } from "lucide-react"
 
 import { vscode } from "@src/utils/vscode"
 import { useExtensionState } from "@src/context/ExtensionStateContext"
 import { useAppTranslation } from "@src/i18n/TranslationContext"
-import { AutoApproveToggle, AutoApproveSetting, autoApproveSettingsConfig } from "../settings/AutoApproveToggle"
-import { StandardTooltip } from "@src/components/ui"
+import { AutoApproveSetting, autoApproveSettingsConfig } from "../settings/AutoApproveToggle"
+import { AutoApproveToggleDropdown } from "./AutoApproveToggleDropdown"
+import { StandardTooltip, Popover, PopoverContent, PopoverTrigger } from "@src/components/ui"
 import { useAutoApprovalState } from "@src/hooks/useAutoApprovalState"
 import { useAutoApprovalToggles } from "@src/hooks/useAutoApprovalToggles"
+import { cn } from "@src/lib/utils"
+import { useRooPortal } from "@src/components/ui/hooks/useRooPortal"
 
 interface AutoApproveMenuProps {
 	style?: React.CSSProperties
@@ -16,6 +20,7 @@ interface AutoApproveMenuProps {
 
 const AutoApproveMenu = ({ style }: AutoApproveMenuProps) => {
 	const [isExpanded, setIsExpanded] = useState(false)
+	const portalContainer = useRooPortal("roo-portal")
 
 	const {
 		autoApprovalEnabled,
@@ -123,10 +128,6 @@ const AutoApproveMenu = ({ style }: AutoApproveMenuProps) => {
 		],
 	)
 
-	const toggleExpanded = useCallback(() => {
-		setIsExpanded((prev) => !prev)
-	}, [])
-
 	const enabledActionsList = Object.entries(toggles)
 		.filter(([_key, value]) => !!value)
 		.map(([key]) => t(autoApproveSettingsConfig[key as AutoApproveSetting].labelKey))
@@ -146,101 +147,118 @@ const AutoApproveMenu = ({ style }: AutoApproveMenuProps) => {
 		[],
 	)
 
+	// Handler for Select All
+	const handleSelectAll = useCallback(() => {
+		const allSettings: AutoApproveSetting[] = Object.keys(toggles) as AutoApproveSetting[]
+		allSettings.forEach((key) => {
+			if (!toggles[key]) {
+				onAutoApproveToggle(key, true)
+			}
+		})
+	}, [toggles, onAutoApproveToggle])
+
+	// Handler for Select None
+	const handleSelectNone = useCallback(() => {
+		const allSettings: AutoApproveSetting[] = Object.keys(toggles) as AutoApproveSetting[]
+		allSettings.forEach((key) => {
+			if (toggles[key]) {
+				onAutoApproveToggle(key, false)
+			}
+		})
+	}, [toggles, onAutoApproveToggle])
+
+	const trigger = (
+		<PopoverTrigger
+			className={cn(
+				"inline-flex items-center gap-1.5 relative whitespace-nowrap px-2 py-1 text-xs",
+				"bg-transparent border border-[rgba(255,255,255,0.08)] rounded-md text-vscode-foreground",
+				"transition-all duration-150 focus:outline-none focus-visible:ring-1 focus-visible:ring-vscode-focusBorder focus-visible:ring-inset",
+				"opacity-90 hover:opacity-100 hover:bg-[rgba(255,255,255,0.03)] hover:border-[rgba(255,255,255,0.15)] cursor-pointer",
+			)}
+			style={style}>
+			<Stamp className="size-3.5 opacity-80 flex-shrink-0" />
+			<span className="font-medium">{t("chat:autoApprove.title")}</span>
+			<span className="text-vscode-descriptionForeground truncate max-w-[200px]">{displayText}</span>
+		</PopoverTrigger>
+	)
+
 	return (
-		<div
-			style={{
-				padding: "0 15px",
-				userSelect: "none",
-				borderTop: isExpanded
-					? `0.5px solid color-mix(in srgb, var(--vscode-titleBar-inactiveForeground) 20%, transparent)`
-					: "none",
-				overflowY: "auto",
-				...style,
-			}}>
-			{isExpanded && (
-				<div className="flex flex-col gap-2 py-4">
-					<div
-						style={{
-							color: "var(--vscode-descriptionForeground)",
-							fontSize: "12px",
-						}}>
-						<Trans
-							i18nKey="chat:autoApprove.description"
-							components={{
-								settingsLink: <VSCodeLink href="#" onClick={handleOpenSettings} />,
-							}}
-						/>
+		<Popover open={isExpanded} onOpenChange={setIsExpanded}>
+			<StandardTooltip content={t("chat:autoApprove.tooltip")}>{trigger}</StandardTooltip>
+
+			<PopoverContent
+				align="start"
+				sideOffset={4}
+				container={portalContainer}
+				className="p-0 overflow-hidden min-w-[400px] max-w-[500px]">
+				<div className="flex flex-col w-full">
+					{/* Header with master toggle */}
+					<div className="flex items-center justify-between p-3 border-b border-vscode-dropdown-border">
+						<div className="flex items-center gap-2">
+							<StandardTooltip
+								content={!hasEnabledOptions ? t("chat:autoApprove.selectOptionsFirst") : undefined}>
+								<VSCodeCheckbox
+									checked={effectiveAutoApprovalEnabled}
+									disabled={!hasEnabledOptions}
+									aria-label={
+										hasEnabledOptions
+											? t("chat:autoApprove.toggleAriaLabel")
+											: t("chat:autoApprove.disabledAriaLabel")
+									}
+									onChange={() => {
+										if (hasEnabledOptions) {
+											const newValue = !(autoApprovalEnabled ?? false)
+											setAutoApprovalEnabled(newValue)
+											vscode.postMessage({ type: "autoApprovalEnabled", bool: newValue })
+										}
+									}}
+								/>
+							</StandardTooltip>
+							<h4 className="m-0 font-medium text-sm">{t("chat:autoApprove.title")}</h4>
+						</div>
+						<div className="flex items-center gap-1">
+							<StandardTooltip content={t("chat:autoApprove.selectAll")}>
+								<button
+									onClick={handleSelectAll}
+									className="p-1 rounded hover:bg-vscode-list-hoverBackground transition-colors">
+									<ListChecks className="size-4" />
+								</button>
+							</StandardTooltip>
+							<StandardTooltip content={t("chat:autoApprove.selectNone")}>
+								<button
+									onClick={handleSelectNone}
+									className="p-1 rounded hover:bg-vscode-list-hoverBackground transition-colors">
+									<LayoutList className="size-4" />
+								</button>
+							</StandardTooltip>
+						</div>
 					</div>
 
-					<AutoApproveToggle {...toggles} onToggle={onAutoApproveToggle} />
-				</div>
-			)}
+					{/* Description */}
+					<div className="px-3 py-2 border-b border-vscode-dropdown-border">
+						<div
+							style={{
+								color: "var(--vscode-descriptionForeground)",
+								fontSize: "12px",
+							}}>
+							<Trans
+								i18nKey="chat:autoApprove.description"
+								components={{
+									settingsLink: <VSCodeLink href="#" onClick={handleOpenSettings} />,
+								}}
+							/>
+						</div>
+					</div>
 
-			<div
-				style={{
-					display: "flex",
-					alignItems: "center",
-					gap: "8px",
-					padding: "2px 0 0 0",
-					cursor: "pointer",
-				}}
-				onClick={toggleExpanded}>
-				<div onClick={(e) => e.stopPropagation()}>
-					<StandardTooltip
-						content={!hasEnabledOptions ? t("chat:autoApprove.selectOptionsFirst") : undefined}>
-						<VSCodeCheckbox
-							checked={effectiveAutoApprovalEnabled}
-							disabled={!hasEnabledOptions}
-							aria-label={
-								hasEnabledOptions
-									? t("chat:autoApprove.toggleAriaLabel")
-									: t("chat:autoApprove.disabledAriaLabel")
-							}
-							onChange={() => {
-								if (hasEnabledOptions) {
-									const newValue = !(autoApprovalEnabled ?? false)
-									setAutoApprovalEnabled(newValue)
-									vscode.postMessage({ type: "autoApprovalEnabled", bool: newValue })
-								}
-								// If no options enabled, do nothing
-							}}
-						/>
-					</StandardTooltip>
+					{/* Two-column layout for toggles */}
+					<div className="p-3 max-h-[400px] overflow-y-auto">
+						<div className="grid grid-cols-2 gap-x-4">
+							<AutoApproveToggleDropdown {...toggles} onToggle={onAutoApproveToggle} />
+						</div>
+					</div>
 				</div>
-				<div
-					style={{
-						display: "flex",
-						alignItems: "center",
-						gap: "4px",
-						flex: 1,
-						minWidth: 0,
-					}}>
-					<span
-						style={{
-							color: "var(--vscode-foreground)",
-							flexShrink: 0,
-						}}>
-						{t("chat:autoApprove.title")}
-					</span>
-					<span
-						style={{
-							color: "var(--vscode-descriptionForeground)",
-							overflow: "hidden",
-							textOverflow: "ellipsis",
-							whiteSpace: "nowrap",
-							flex: 1,
-							minWidth: 0,
-						}}>
-						{displayText}
-					</span>
-					<span
-						className={`codicon codicon-chevron-right flex-shrink-0 transition-transform duration-200 ease-in-out ${
-							isExpanded ? "-rotate-90 ml-[2px]" : "rotate-0 -ml-[2px]"
-						}`}
-					/>
-				</div>
-			</div>
-		</div>
+			</PopoverContent>
+		</Popover>
 	)
 }
 
diff --git a/webview-ui/src/components/chat/AutoApproveToggleDropdown.tsx b/webview-ui/src/components/chat/AutoApproveToggleDropdown.tsx
new file mode 100644
index 0000000000..279194593a
--- /dev/null
+++ b/webview-ui/src/components/chat/AutoApproveToggleDropdown.tsx
@@ -0,0 +1,73 @@
+import type { GlobalSettings } from "@roo-code/types"
+import { useAppTranslation } from "@/i18n/TranslationContext"
+import { cn } from "@/lib/utils"
+import { StandardTooltip } from "@/components/ui"
+import { autoApproveSettingsConfig, AutoApproveSetting } from "../settings/AutoApproveToggle"
+
+type AutoApproveToggles = Pick<
+	GlobalSettings,
+	| "alwaysAllowReadOnly"
+	| "alwaysAllowWrite"
+	| "alwaysAllowBrowser"
+	| "alwaysApproveResubmit"
+	| "alwaysAllowMcp"
+	| "alwaysAllowModeSwitch"
+	| "alwaysAllowSubtasks"
+	| "alwaysAllowExecute"
+	| "alwaysAllowFollowupQuestions"
+	| "alwaysAllowUpdateTodoList"
+>
+
+type AutoApproveToggleDropdownProps = AutoApproveToggles & {
+	onToggle: (key: AutoApproveSetting, value: boolean) => void
+}
+
+export const AutoApproveToggleDropdown = ({ onToggle, ...props }: AutoApproveToggleDropdownProps) => {
+	const { t } = useAppTranslation()
+
+	// Split settings into two columns for better layout
+	const settings = Object.values(autoApproveSettingsConfig)
+	const halfLength = Math.ceil(settings.length / 2)
+	const leftColumn = settings.slice(0, halfLength)
+	const rightColumn = settings.slice(halfLength)
+
+	const renderToggleItem = ({
+		key,
+		descriptionKey,
+		labelKey,
+		icon,
+		testId,
+	}: (typeof autoApproveSettingsConfig)[AutoApproveSetting]) => (
+		<StandardTooltip key={key} content={t(descriptionKey || "")}>
+			<button
+				onClick={() => onToggle(key, !props[key])}
+				aria-label={t(labelKey)}
+				aria-pressed={!!props[key]}
+				data-testid={testId}
+				className={cn(
+					"w-full flex items-center gap-2 px-2 py-1.5 rounded text-xs text-left",
+					"transition-colors hover:bg-vscode-list-hoverBackground",
+					props[key]
+						? "bg-vscode-list-activeSelectionBackground text-vscode-list-activeSelectionForeground"
+						: "opacity-70",
+				)}>
+				<span className={cn("codicon", `codicon-${icon}`, "text-sm flex-shrink-0")} />
+				<span className="flex-1 truncate">{t(labelKey)}</span>
+				<span
+					className={cn(
+						"text-[10px] px-1 rounded",
+						props[key] ? "bg-vscode-badge-background text-vscode-badge-foreground" : "",
+					)}>
+					{props[key] ? "✓" : ""}
+				</span>
+			</button>
+		</StandardTooltip>
+	)
+
+	return (
+		<>
+			<div className="flex flex-col gap-1">{leftColumn.map(renderToggleItem)}</div>
+			<div className="flex flex-col gap-1">{rightColumn.map(renderToggleItem)}</div>
+		</>
+	)
+}
diff --git a/webview-ui/src/components/chat/ChatView.tsx b/webview-ui/src/components/chat/ChatView.tsx
index 44eeb33b66..3cd10138e8 100644
--- a/webview-ui/src/components/chat/ChatView.tsx
+++ b/webview-ui/src/components/chat/ChatView.tsx
@@ -1882,11 +1882,6 @@ const ChatViewComponent: React.ForwardRefRenderFunction<ChatViewRef, ChatViewPro
 			//    This ensures it takes its natural height when there's space
 			//    but becomes scrollable when the viewport is too small
 			*/}
-			{!task && (
-				<div className="mb-1 flex-initial min-h-0">
-					<AutoApproveMenu />
-				</div>
-			)}
 
 			{task && (
 				<>
@@ -1909,9 +1904,6 @@ const ChatViewComponent: React.ForwardRefRenderFunction<ChatViewRef, ChatViewPro
 							initialTopMostItemIndex={groupedMessages.length - 1}
 						/>
 					</div>
-					<div className={`flex-initial min-h-0 ${!areButtonsVisible ? "mb-1" : ""}`}>
-						<AutoApproveMenu />
-					</div>
 					{areButtonsVisible && (
 						<div
 							className={`flex h-9 items-center mb-1 px-[15px] ${
@@ -2025,6 +2017,11 @@ const ChatViewComponent: React.ForwardRefRenderFunction<ChatViewRef, ChatViewPro
 				modeShortcutText={modeShortcutText}
 			/>
 
+			{/* Auto-Approve Menu positioned below text area */}
+			<div className="px-3 pb-2">
+				<AutoApproveMenu />
+			</div>
+
 			{isProfileDisabled && (
 				<div className="px-3">
 					<ProfileViolationWarning />
diff --git a/webview-ui/src/components/chat/__tests__/AutoApproveMenu.spec.tsx b/webview-ui/src/components/chat/__tests__/AutoApproveMenu.spec.tsx
index 185e5eeec6..0c185fec4d 100644
--- a/webview-ui/src/components/chat/__tests__/AutoApproveMenu.spec.tsx
+++ b/webview-ui/src/components/chat/__tests__/AutoApproveMenu.spec.tsx
@@ -115,7 +115,7 @@ describe("AutoApproveMenu", () => {
 			expect(screen.getByText("Read-only operations")).toBeInTheDocument()
 		})
 
-		it("should not allow toggling master checkbox when no options are selected", () => {
+		it("should not allow toggling master checkbox when no options are selected", async () => {
 			;(useExtensionState as ReturnType<typeof vi.fn>).mockReturnValue({
 				...defaultExtensionState,
 				autoApprovalEnabled: false,
@@ -124,6 +124,15 @@ describe("AutoApproveMenu", () => {
 
 			render(<AutoApproveMenu />)
 
+			// Click to open the dropdown
+			const trigger = screen.getByText("Auto-approve")
+			fireEvent.click(trigger)
+
+			// Wait for the dropdown to open
+			await waitFor(() => {
+				expect(screen.getByRole("checkbox")).toBeInTheDocument()
+			})
+
 			// Click on the master checkbox
 			const masterCheckbox = screen.getByRole("checkbox")
 			fireEvent.click(masterCheckbox)
@@ -132,7 +141,7 @@ describe("AutoApproveMenu", () => {
 			expect(mockPostMessage).not.toHaveBeenCalled()
 		})
 
-		it("should toggle master checkbox when options are selected", () => {
+		it("should toggle master checkbox when options are selected", async () => {
 			;(useExtensionState as ReturnType<typeof vi.fn>).mockReturnValue({
 				...defaultExtensionState,
 				autoApprovalEnabled: true,
@@ -141,6 +150,15 @@ describe("AutoApproveMenu", () => {
 
 			render(<AutoApproveMenu />)
 
+			// Click to open the dropdown
+			const trigger = screen.getByText("Auto-approve")
+			fireEvent.click(trigger)
+
+			// Wait for the dropdown to open
+			await waitFor(() => {
+				expect(screen.getByRole("checkbox")).toBeInTheDocument()
+			})
+
 			// Click on the master checkbox
 			const masterCheckbox = screen.getByRole("checkbox")
 			fireEvent.click(masterCheckbox)
@@ -164,9 +182,9 @@ describe("AutoApproveMenu", () => {
 
 			render(<AutoApproveMenu />)
 
-			// Expand the menu
-			const menuContainer = screen.getByText("Auto-approve").parentElement
-			fireEvent.click(menuContainer!)
+			// Click to open the dropdown
+			const trigger = screen.getByText("Auto-approve")
+			fireEvent.click(trigger)
 
 			// Wait for the menu to expand and find the read-only button
 			await waitFor(() => {
@@ -192,9 +210,9 @@ describe("AutoApproveMenu", () => {
 
 			render(<AutoApproveMenu />)
 
-			// Expand the menu
-			const menuContainer = screen.getByText("Auto-approve").parentElement
-			fireEvent.click(menuContainer!)
+			// Click to open the dropdown
+			const trigger = screen.getByText("Auto-approve")
+			fireEvent.click(trigger)
 
 			await waitFor(() => {
 				expect(screen.getByTestId("always-allow-write-toggle")).toBeInTheDocument()
@@ -240,9 +258,9 @@ describe("AutoApproveMenu", () => {
 
 			render(<AutoApproveMenu />)
 
-			// Expand the menu
-			const menuContainer = screen.getByText("Auto-approve").parentElement
-			fireEvent.click(menuContainer!)
+			// Click to open the dropdown
+			const trigger = screen.getByText("Auto-approve")
+			fireEvent.click(trigger)
 
 			await waitFor(() => {
 				expect(screen.getByTestId("always-allow-readonly-toggle")).toBeInTheDocument()
@@ -279,9 +297,9 @@ describe("AutoApproveMenu", () => {
 
 			render(<AutoApproveMenu />)
 
-			// Expand the menu
-			const menuContainer = screen.getByText("Auto-approve").parentElement
-			fireEvent.click(menuContainer!)
+			// Click to open the dropdown
+			const trigger = screen.getByText("Auto-approve")
+			fireEvent.click(trigger)
 
 			await waitFor(() => {
 				expect(screen.getByTestId("always-allow-readonly-toggle")).toBeInTheDocument()