diff --git a/webview-ui/src/components/chat/ChatTextArea.tsx b/webview-ui/src/components/chat/ChatTextArea.tsx
index 58f42a367b..45b786b9cf 100644
--- a/webview-ui/src/components/chat/ChatTextArea.tsx
+++ b/webview-ui/src/components/chat/ChatTextArea.tsx
@@ -30,6 +30,7 @@ import { AutoApproveDropdown } from "./AutoApproveDropdown"
 import { MAX_IMAGES_PER_MESSAGE } from "./ChatView"
 import ContextMenu from "./ContextMenu"
 import { IndexingStatusBadge } from "./IndexingStatusBadge"
+import { TaskHistoryWarning } from "./TaskHistoryWarning"
 import { usePromptHistory } from "./hooks/usePromptHistory"
 import { CloudAccountSwitcher } from "../cloud/CloudAccountSwitcher"
 
@@ -1265,6 +1266,7 @@ export const ChatTextArea = forwardRef<HTMLTextAreaElement, ChatTextAreaProps>(
 							</StandardTooltip>
 						)}
 						{!isEditMode ? <IndexingStatusBadge /> : null}
+						{!isEditMode ? <TaskHistoryWarning /> : null}
 						{!isEditMode && cloudUserInfo && <CloudAccountSwitcher />}
 						{/* keep props referenced after moving browser button */}
 						<div
diff --git a/webview-ui/src/components/chat/TaskHistoryWarning.tsx b/webview-ui/src/components/chat/TaskHistoryWarning.tsx
new file mode 100644
index 0000000000..75fd9660d4
--- /dev/null
+++ b/webview-ui/src/components/chat/TaskHistoryWarning.tsx
@@ -0,0 +1,212 @@
+import React, { useState, useEffect, useMemo } from "react"
+import { AlertTriangle, X, Trash2 } from "lucide-react"
+
+import { cn } from "@src/lib/utils"
+import { vscode } from "@src/utils/vscode"
+import { useAppTranslation } from "@/i18n/TranslationContext"
+import { useExtensionState } from "@src/context/ExtensionStateContext"
+import {
+	Popover,
+	PopoverContent,
+	PopoverTrigger,
+	StandardTooltip,
+	Button,
+	AlertDialog,
+	AlertDialogAction,
+	AlertDialogCancel,
+	AlertDialogContent,
+	AlertDialogDescription,
+	AlertDialogFooter,
+	AlertDialogHeader,
+	AlertDialogTitle,
+} from "@src/components/ui"
+
+interface TaskHistoryWarningProps {
+	className?: string
+}
+
+const TASK_WARNING_THRESHOLD = 1000
+const TASK_WARNING_INCREMENT = 1000
+const CLEANUP_DAYS_THRESHOLD = 30
+
+export const TaskHistoryWarning: React.FC<TaskHistoryWarningProps> = ({ className }) => {
+	const { t } = useAppTranslation()
+	const { taskHistory } = useExtensionState()
+
+	const [dismissedAtTaskCount, setDismissedAtTaskCount] = useState<number>(0)
+	const [showCleanupDialog, setShowCleanupDialog] = useState(false)
+	const [isCleaningUp, setIsCleaningUp] = useState(false)
+
+	// Load dismissed state from localStorage
+	useEffect(() => {
+		const stored = localStorage.getItem("taskHistoryWarningDismissed")
+		if (stored) {
+			setDismissedAtTaskCount(parseInt(stored, 10))
+		}
+	}, [])
+
+	// Calculate task count and whether to show warning
+	const taskCount = useMemo(() => {
+		return taskHistory?.length || 0
+	}, [taskHistory])
+
+	const shouldShowWarning = useMemo(() => {
+		if (taskCount < TASK_WARNING_THRESHOLD) {
+			return false
+		}
+
+		// Show warning if we've crossed a new threshold since dismissal
+		const currentThreshold = Math.floor(taskCount / TASK_WARNING_INCREMENT) * TASK_WARNING_INCREMENT
+		const dismissedThreshold = Math.floor(dismissedAtTaskCount / TASK_WARNING_INCREMENT) * TASK_WARNING_INCREMENT
+
+		return currentThreshold > dismissedThreshold
+	}, [taskCount, dismissedAtTaskCount])
+
+	// Calculate how many tasks would be deleted
+	const tasksToDelete = useMemo(() => {
+		if (!taskHistory) return 0
+
+		const cutoffDate = Date.now() - CLEANUP_DAYS_THRESHOLD * 24 * 60 * 60 * 1000
+		return taskHistory.filter((task) => task.ts < cutoffDate).length
+	}, [taskHistory])
+
+	const handleDismiss = () => {
+		setDismissedAtTaskCount(taskCount)
+		localStorage.setItem("taskHistoryWarningDismissed", taskCount.toString())
+	}
+
+	const handleCleanup = async () => {
+		if (isCleaningUp) return
+
+		setIsCleaningUp(true)
+		setShowCleanupDialog(false)
+
+		try {
+			// Get tasks older than 30 days
+			const cutoffDate = Date.now() - CLEANUP_DAYS_THRESHOLD * 24 * 60 * 60 * 1000
+			const tasksToDelete = taskHistory?.filter((task) => task.ts < cutoffDate).map((task) => task.id) || []
+
+			if (tasksToDelete.length > 0) {
+				// Send message to delete tasks
+				vscode.postMessage({
+					type: "deleteMultipleTasksWithIds",
+					ids: tasksToDelete,
+				})
+
+				// Reset dismissed state since we've cleaned up
+				setDismissedAtTaskCount(0)
+				localStorage.removeItem("taskHistoryWarningDismissed")
+			}
+		} finally {
+			setIsCleaningUp(false)
+		}
+	}
+
+	if (!shouldShowWarning) {
+		return null
+	}
+
+	return (
+		<>
+			<Popover>
+				<StandardTooltip content={t("chat:taskHistoryWarning.tooltip", { count: taskCount })}>
+					<PopoverTrigger asChild>
+						<Button
+							variant="ghost"
+							size="sm"
+							aria-label={t("chat:taskHistoryWarning.ariaLabel")}
+							className={cn(
+								"relative h-5 w-5 p-0",
+								"text-yellow-500 opacity-85",
+								"hover:opacity-100 hover:bg-[rgba(255,255,255,0.03)]",
+								"focus:outline-none focus-visible:ring-1 focus-visible:ring-vscode-focusBorder",
+								"animate-pulse",
+								className,
+							)}>
+							<AlertTriangle className="w-4 h-4" />
+							{taskCount >= 2000 && (
+								<span className="absolute -top-1 -right-1 w-2 h-2 bg-red-500 rounded-full" />
+							)}
+						</Button>
+					</PopoverTrigger>
+				</StandardTooltip>
+
+				<PopoverContent className="w-80 p-4" align="end">
+					<div className="space-y-3">
+						<div className="flex items-start justify-between">
+							<div className="flex items-center gap-2">
+								<AlertTriangle className="w-4 h-4 text-yellow-500 flex-shrink-0 mt-0.5" />
+								<h3 className="font-semibold text-sm">{t("chat:taskHistoryWarning.title")}</h3>
+							</div>
+							<Button
+								variant="ghost"
+								size="sm"
+								onClick={handleDismiss}
+								className="h-5 w-5 p-0 opacity-60 hover:opacity-100"
+								aria-label={t("chat:taskHistoryWarning.dismiss")}>
+								<X className="w-3 h-3" />
+							</Button>
+						</div>
+
+						<div className="text-sm text-vscode-descriptionForeground">
+							<p className="mb-2">{t("chat:taskHistoryWarning.message", { count: taskCount })}</p>
+							<p className="text-xs opacity-80">{t("chat:taskHistoryWarning.performance")}</p>
+						</div>
+
+						<div className="flex flex-col gap-2">
+							<Button
+								variant="primary"
+								size="sm"
+								onClick={() => setShowCleanupDialog(true)}
+								disabled={isCleaningUp || tasksToDelete === 0}
+								className="w-full">
+								<Trash2 className="w-3 h-3 mr-2" />
+								{isCleaningUp
+									? t("chat:taskHistoryWarning.cleaning")
+									: tasksToDelete > 0
+										? t("chat:taskHistoryWarning.cleanupButton", { count: tasksToDelete })
+										: t("chat:taskHistoryWarning.noOldTasks")}
+							</Button>
+
+							{tasksToDelete === 0 && taskCount > TASK_WARNING_THRESHOLD && (
+								<p className="text-xs text-center text-vscode-descriptionForeground opacity-70">
+									{t("chat:taskHistoryWarning.allRecent")}
+								</p>
+							)}
+						</div>
+					</div>
+				</PopoverContent>
+			</Popover>
+
+			<AlertDialog open={showCleanupDialog} onOpenChange={setShowCleanupDialog}>
+				<AlertDialogContent className="max-w-md">
+					<AlertDialogHeader>
+						<AlertDialogTitle>{t("chat:taskHistoryWarning.confirmTitle")}</AlertDialogTitle>
+						<AlertDialogDescription className="text-vscode-foreground">
+							<div className="mb-2">
+								{t("chat:taskHistoryWarning.confirmMessage", {
+									count: tasksToDelete,
+									days: CLEANUP_DAYS_THRESHOLD,
+								})}
+							</div>
+							<div className="text-vscode-editor-foreground bg-vscode-editor-background p-2 rounded text-sm">
+								{t("chat:taskHistoryWarning.confirmWarning")}
+							</div>
+						</AlertDialogDescription>
+					</AlertDialogHeader>
+					<AlertDialogFooter>
+						<AlertDialogCancel asChild>
+							<Button variant="secondary">{t("common:cancel")}</Button>
+						</AlertDialogCancel>
+						<AlertDialogAction asChild>
+							<Button variant="destructive" onClick={handleCleanup}>
+								<Trash2 className="w-3 h-3 mr-2" />
+								{t("chat:taskHistoryWarning.confirmButton")}
+							</Button>
+						</AlertDialogAction>
+					</AlertDialogFooter>
+				</AlertDialogContent>
+			</AlertDialog>
+		</>
+	)
+}
diff --git a/webview-ui/src/components/chat/__tests__/TaskHistoryWarning.spec.tsx b/webview-ui/src/components/chat/__tests__/TaskHistoryWarning.spec.tsx
new file mode 100644
index 0000000000..40075aee0c
--- /dev/null
+++ b/webview-ui/src/components/chat/__tests__/TaskHistoryWarning.spec.tsx
@@ -0,0 +1,222 @@
+import { render, screen, fireEvent, waitFor } from "@testing-library/react"
+import { describe, it, expect, vi, beforeEach } from "vitest"
+import { TaskHistoryWarning } from "../TaskHistoryWarning"
+
+vi.mock("@/i18n/TranslationContext", () => ({
+	useAppTranslation: () => ({
+		t: (key: string, params?: any) => {
+			const translations: Record<string, string> = {
+				"chat:taskHistoryWarning.title": "High Task History",
+				"chat:taskHistoryWarning.description": `You have ${params?.count || 0} tasks in your history. Consider cleaning up old tasks to improve performance.`,
+				"chat:taskHistoryWarning.cleanupButton": "Clean up tasks older than 30 days",
+				"chat:taskHistoryWarning.dismiss": "Dismiss",
+				"chat:taskHistoryWarning.cleanupDialog.title": "Clean Up Old Tasks",
+				"chat:taskHistoryWarning.cleanupDialog.description": `This will permanently delete all tasks older than 30 days (${params?.count || 0} tasks). This action cannot be undone.`,
+				"chat:taskHistoryWarning.cleanupDialog.cancel": "Cancel",
+				"chat:taskHistoryWarning.cleanupDialog.confirm": "Clean Up",
+				"chat:taskHistoryWarning.cleanupSuccess": `Successfully deleted ${params?.count || 0} old tasks`,
+				"chat:taskHistoryWarning.cleanupError": `Failed to clean up tasks: ${params?.error || "Unknown error"}`,
+			}
+			return translations[key] || key
+		},
+	}),
+}))
+
+const mockTaskHistory: any[] = []
+const mockSetTaskHistory = vi.fn()
+
+vi.mock("@src/context/ExtensionStateContext", () => ({
+	useExtensionState: () => ({
+		taskHistory: mockTaskHistory,
+		setTaskHistory: mockSetTaskHistory,
+	}),
+}))
+
+const mockPostMessage = vi.fn()
+vi.mock("@src/utils/vscode", () => ({
+	vscode: {
+		postMessage: mockPostMessage,
+	},
+}))
+
+const localStorageMock = {
+	getItem: vi.fn(),
+	setItem: vi.fn(),
+	removeItem: vi.fn(),
+	clear: vi.fn(),
+}
+Object.defineProperty(window, "localStorage", {
+	value: localStorageMock,
+	writable: true,
+})
+
+describe("TaskHistoryWarning", () => {
+	beforeEach(() => {
+		vi.clearAllMocks()
+		localStorageMock.getItem.mockReturnValue(null)
+		mockTaskHistory.length = 0
+	})
+
+	it("should not render when task history is below threshold", () => {
+		mockTaskHistory.push(...Array(999).fill({ id: "task" }))
+
+		const { container } = render(<TaskHistoryWarning />)
+		expect(container.firstChild).toBeNull()
+	})
+
+	it("should render warning when task history exceeds threshold", () => {
+		mockTaskHistory.push(...Array(1001).fill({ id: "task" }))
+
+		render(<TaskHistoryWarning />)
+
+		const warningButton = screen.getByRole("button", { name: /High Task History/i })
+		expect(warningButton).toBeInTheDocument()
+	})
+
+	it("should not render if dismissed at current threshold", () => {
+		mockTaskHistory.push(...Array(1500).fill({ id: "task" }))
+
+		localStorageMock.getItem.mockReturnValue("1000")
+
+		const { container } = render(<TaskHistoryWarning />)
+		expect(container.firstChild).toBeNull()
+	})
+
+	it("should render if task count exceeds next threshold after dismissal", () => {
+		mockTaskHistory.push(...Array(2001).fill({ id: "task" }))
+
+		localStorageMock.getItem.mockReturnValue("1000")
+
+		render(<TaskHistoryWarning />)
+
+		const warningButton = screen.getByRole("button", { name: /High Task History/i })
+		expect(warningButton).toBeInTheDocument()
+	})
+
+	it("should show popover content when warning button is clicked", () => {
+		mockTaskHistory.push(...Array(1001).fill({ id: "task" }))
+
+		render(<TaskHistoryWarning />)
+
+		const warningButton = screen.getByRole("button", { name: /High Task History/i })
+		fireEvent.click(warningButton)
+
+		expect(screen.getByText(/You have 1001 tasks in your history/)).toBeInTheDocument()
+		expect(screen.getByText("Clean up tasks older than 30 days")).toBeInTheDocument()
+		expect(screen.getByText("Dismiss")).toBeInTheDocument()
+	})
+
+	it("should dismiss warning and save to localStorage", () => {
+		mockTaskHistory.push(...Array(1001).fill({ id: "task" }))
+
+		render(<TaskHistoryWarning />)
+
+		const warningButton = screen.getByRole("button", { name: /High Task History/i })
+		fireEvent.click(warningButton)
+
+		const dismissButton = screen.getByText("Dismiss")
+		fireEvent.click(dismissButton)
+
+		expect(localStorageMock.setItem).toHaveBeenCalledWith("taskHistoryWarningDismissedThreshold", "1000")
+	})
+
+	it("should show cleanup confirmation dialog when cleanup button is clicked", async () => {
+		const now = Date.now()
+		const oldDate = now - 31 * 24 * 60 * 60 * 1000
+		const newDate = now - 10 * 24 * 60 * 60 * 1000
+
+		mockTaskHistory.push(
+			...Array(500).fill({ id: "old", ts: oldDate }),
+			...Array(501).fill({ id: "new", ts: newDate }),
+		)
+
+		render(<TaskHistoryWarning />)
+
+		const warningButton = screen.getByRole("button", { name: /High Task History/i })
+		fireEvent.click(warningButton)
+
+		const cleanupButton = screen.getByText("Clean up tasks older than 30 days")
+		fireEvent.click(cleanupButton)
+
+		await waitFor(() => {
+			expect(screen.getByText("Clean Up Old Tasks")).toBeInTheDocument()
+			expect(screen.getByText(/This will permanently delete all tasks older than 30 days/)).toBeInTheDocument()
+		})
+	})
+
+	it("should call deleteMultipleTasksWithIds when cleanup is confirmed", async () => {
+		const now = Date.now()
+		const oldDate = now - 31 * 24 * 60 * 60 * 1000
+		const newDate = now - 10 * 24 * 60 * 60 * 1000
+
+		mockTaskHistory.push({ id: "old1", ts: oldDate }, { id: "old2", ts: oldDate }, { id: "new1", ts: newDate })
+
+		render(<TaskHistoryWarning />)
+
+		const warningButton = screen.getByRole("button", { name: /High Task History/i })
+		fireEvent.click(warningButton)
+
+		const cleanupButton = screen.getByText("Clean up tasks older than 30 days")
+		fireEvent.click(cleanupButton)
+
+		await waitFor(() => {
+			const confirmButton = screen.getByRole("button", { name: "Clean Up" })
+			fireEvent.click(confirmButton)
+		})
+
+		expect(mockPostMessage).toHaveBeenCalledWith({
+			type: "deleteMultipleTasksWithIds",
+			ids: ["old1", "old2"],
+		})
+	})
+
+	it("should handle cleanup with no old tasks gracefully", async () => {
+		const now = Date.now()
+		const newDate = now - 10 * 24 * 60 * 60 * 1000
+
+		mockTaskHistory.push(...Array(1001).fill({ id: "new", ts: newDate }))
+
+		render(<TaskHistoryWarning />)
+
+		const warningButton = screen.getByRole("button", { name: /High Task History/i })
+		fireEvent.click(warningButton)
+
+		const cleanupButton = screen.getByText("Clean up tasks older than 30 days")
+		fireEvent.click(cleanupButton)
+
+		await waitFor(() => {
+			expect(screen.getByText(/\(0 tasks\)/)).toBeInTheDocument()
+		})
+	})
+
+	it("should apply custom className when provided", () => {
+		mockTaskHistory.push(...Array(1001).fill({ id: "task" }))
+
+		const { container } = render(<TaskHistoryWarning className="custom-class" />)
+
+		const wrapper = container.firstChild as HTMLElement
+		expect(wrapper).toHaveClass("custom-class")
+	})
+
+	it("should handle tasks without timestamps", async () => {
+		mockTaskHistory.push({ id: "no-ts-1" }, { id: "no-ts-2" }, ...Array(999).fill({ id: "task", ts: Date.now() }))
+
+		render(<TaskHistoryWarning />)
+
+		const warningButton = screen.getByRole("button", { name: /High Task History/i })
+		fireEvent.click(warningButton)
+
+		const cleanupButton = screen.getByText("Clean up tasks older than 30 days")
+		fireEvent.click(cleanupButton)
+
+		await waitFor(() => {
+			const confirmButton = screen.getByRole("button", { name: "Clean Up" })
+			fireEvent.click(confirmButton)
+		})
+
+		expect(mockPostMessage).toHaveBeenCalledWith({
+			type: "deleteMultipleTasksWithIds",
+			ids: expect.arrayContaining(["no-ts-1", "no-ts-2"]),
+		})
+	})
+})
diff --git a/webview-ui/src/i18n/locales/en/chat.json b/webview-ui/src/i18n/locales/en/chat.json
index 6a0f7f8e15..ee7e530037 100644
--- a/webview-ui/src/i18n/locales/en/chat.json
+++ b/webview-ui/src/i18n/locales/en/chat.json
@@ -425,5 +425,19 @@
 		"updated": "Updated the to-do list",
 		"completed": "Completed",
 		"started": "Started"
+	},
+	"taskHistoryWarning": {
+		"title": "High Task History",
+		"description": "You have {{count}} tasks in your history. Consider cleaning up old tasks to improve performance.",
+		"cleanupButton": "Clean up tasks older than 30 days",
+		"dismiss": "Dismiss",
+		"cleanupDialog": {
+			"title": "Clean Up Old Tasks",
+			"description": "This will permanently delete all tasks older than 30 days ({{count}} tasks). This action cannot be undone.",
+			"cancel": "Cancel",
+			"confirm": "Clean Up"
+		},
+		"cleanupSuccess": "Successfully deleted {{count}} old tasks",
+		"cleanupError": "Failed to clean up tasks: {{error}}"
 	}
 }