diff --git a/packages/types/src/history.ts b/packages/types/src/history.ts
index 8c75024879c..a11a3f21614 100644
--- a/packages/types/src/history.ts
+++ b/packages/types/src/history.ts
@@ -16,6 +16,7 @@ export const historyItemSchema = z.object({
 	totalCost: z.number(),
 	size: z.number().optional(),
 	workspace: z.string().optional(),
+	starred: z.boolean().optional(),
 })
 
 export type HistoryItem = z.infer<typeof historyItemSchema>
diff --git a/src/core/webview/webviewMessageHandler.ts b/src/core/webview/webviewMessageHandler.ts
index 82c780adf47..29979b163d9 100644
--- a/src/core/webview/webviewMessageHandler.ts
+++ b/src/core/webview/webviewMessageHandler.ts
@@ -440,6 +440,17 @@ export const webviewMessageHandler = async (
 		case "deleteTaskWithId":
 			provider.deleteTaskWithId(message.text!)
 			break
+		case "toggleTaskStar":
+			if (message.text) {
+				const taskHistory = provider.getValue("taskHistory") || []
+				const taskIndex = taskHistory.findIndex((task) => task.id === message.text)
+				if (taskIndex !== -1) {
+					taskHistory[taskIndex].starred = !taskHistory[taskIndex].starred
+					await provider.setValue("taskHistory", taskHistory)
+					await provider.postStateToWebview()
+				}
+			}
+			break
 		case "deleteMultipleTasksWithIds": {
 			const ids = message.ids
 
diff --git a/src/shared/WebviewMessage.ts b/src/shared/WebviewMessage.ts
index 795e2765222..88e7a7a4fcf 100644
--- a/src/shared/WebviewMessage.ts
+++ b/src/shared/WebviewMessage.ts
@@ -59,6 +59,7 @@ export interface WebviewMessage {
 		| "deleteTaskWithId"
 		| "exportTaskWithId"
 		| "importSettings"
+		| "toggleTaskStar"
 		| "exportSettings"
 		| "resetState"
 		| "flushRouterModels"
diff --git a/webview-ui/src/components/history/BatchDeleteTaskDialog.tsx b/webview-ui/src/components/history/BatchDeleteTaskDialog.tsx
index decc905315a..68aa9922b59 100644
--- a/webview-ui/src/components/history/BatchDeleteTaskDialog.tsx
+++ b/webview-ui/src/components/history/BatchDeleteTaskDialog.tsx
@@ -1,4 +1,4 @@
-import { useCallback } from "react"
+import { useCallback, useMemo } from "react"
 import { useAppTranslation } from "@/i18n/TranslationContext"
 import {
 	AlertDialog,
@@ -13,6 +13,7 @@ import {
 } from "@/components/ui"
 import { vscode } from "@/utils/vscode"
 import { AlertDialogProps } from "@radix-ui/react-alert-dialog"
+import { useExtensionState } from "@/context/ExtensionStateContext"
 
 interface BatchDeleteTaskDialogProps extends AlertDialogProps {
 	taskIds: string[]
@@ -21,13 +22,31 @@ interface BatchDeleteTaskDialogProps extends AlertDialogProps {
 export const BatchDeleteTaskDialog = ({ taskIds, ...props }: BatchDeleteTaskDialogProps) => {
 	const { t } = useAppTranslation()
 	const { onOpenChange } = props
+	const { taskHistory } = useExtensionState()
+
+	// Filter out starred tasks
+	const { deletableTaskIds, starredCount } = useMemo(() => {
+		const deletable: string[] = []
+		let starred = 0
+
+		taskIds.forEach((id) => {
+			const task = taskHistory.find((item) => item.id === id)
+			if (task?.starred) {
+				starred++
+			} else {
+				deletable.push(id)
+			}
+		})
+
+		return { deletableTaskIds: deletable, starredCount: starred }
+	}, [taskIds, taskHistory])
 
 	const onDelete = useCallback(() => {
-		if (taskIds.length > 0) {
-			vscode.postMessage({ type: "deleteMultipleTasksWithIds", ids: taskIds })
+		if (deletableTaskIds.length > 0) {
+			vscode.postMessage({ type: "deleteMultipleTasksWithIds", ids: deletableTaskIds })
 			onOpenChange?.(false)
 		}
-	}, [taskIds, onOpenChange])
+	}, [deletableTaskIds, onOpenChange])
 
 	return (
 		<AlertDialog {...props}>
@@ -35,22 +54,41 @@ export const BatchDeleteTaskDialog = ({ taskIds, ...props }: BatchDeleteTaskDial
 				<AlertDialogHeader>
 					<AlertDialogTitle>{t("history:deleteTasks")}</AlertDialogTitle>
 					<AlertDialogDescription className="text-vscode-foreground">
-						<div className="mb-2">{t("history:confirmDeleteTasks", { count: taskIds.length })}</div>
-						<div className="text-vscode-editor-foreground bg-vscode-editor-background p-2 rounded text-sm">
-							{t("history:deleteTasksWarning")}
-						</div>
+						{starredCount > 0 ? (
+							<>
+								<div className="mb-2 text-vscode-notificationsWarningIcon-foreground">
+									{t("history:starredTasksExcluded", { count: starredCount })}
+								</div>
+								{deletableTaskIds.length > 0 && (
+									<div className="mb-2">
+										{t("history:confirmDeleteTasks", { count: deletableTaskIds.length })}
+									</div>
+								)}
+							</>
+						) : (
+							<div className="mb-2">
+								{t("history:confirmDeleteTasks", { count: deletableTaskIds.length })}
+							</div>
+						)}
+						{deletableTaskIds.length > 0 && (
+							<div className="text-vscode-editor-foreground bg-vscode-editor-background p-2 rounded text-sm">
+								{t("history:deleteTasksWarning")}
+							</div>
+						)}
 					</AlertDialogDescription>
 				</AlertDialogHeader>
 				<AlertDialogFooter>
 					<AlertDialogCancel asChild>
 						<Button variant="secondary">{t("history:cancel")}</Button>
 					</AlertDialogCancel>
-					<AlertDialogAction asChild>
-						<Button variant="destructive" onClick={onDelete}>
-							<span className="codicon codicon-trash mr-1"></span>
-							{t("history:deleteItems", { count: taskIds.length })}
-						</Button>
-					</AlertDialogAction>
+					{deletableTaskIds.length > 0 && (
+						<AlertDialogAction asChild>
+							<Button variant="destructive" onClick={onDelete}>
+								<span className="codicon codicon-trash mr-1"></span>
+								{t("history:deleteItems", { count: deletableTaskIds.length })}
+							</Button>
+						</AlertDialogAction>
+					)}
 				</AlertDialogFooter>
 			</AlertDialogContent>
 		</AlertDialog>
diff --git a/webview-ui/src/components/history/DeleteTaskDialog.tsx b/webview-ui/src/components/history/DeleteTaskDialog.tsx
index d0e3ab16a4d..21964a68ef1 100644
--- a/webview-ui/src/components/history/DeleteTaskDialog.tsx
+++ b/webview-ui/src/components/history/DeleteTaskDialog.tsx
@@ -14,6 +14,7 @@ import {
 	Button,
 } from "@/components/ui"
 import { useAppTranslation } from "@/i18n/TranslationContext"
+import { useExtensionState } from "@/context/ExtensionStateContext"
 
 import { vscode } from "@/utils/vscode"
 
@@ -24,9 +25,14 @@ interface DeleteTaskDialogProps extends AlertDialogProps {
 export const DeleteTaskDialog = ({ taskId, ...props }: DeleteTaskDialogProps) => {
 	const { t } = useAppTranslation()
 	const [isEnterPressed] = useKeyPress("Enter")
+	const { taskHistory } = useExtensionState()
 
 	const { onOpenChange } = props
 
+	// Check if the task is starred
+	const task = taskHistory.find((item) => item.id === taskId)
+	const isStarred = task?.starred || false
+
 	const onDelete = useCallback(() => {
 		if (taskId) {
 			vscode.postMessage({ type: "deleteTaskWithId", text: taskId })
@@ -35,27 +41,33 @@ export const DeleteTaskDialog = ({ taskId, ...props }: DeleteTaskDialogProps) =>
 	}, [taskId, onOpenChange])
 
 	useEffect(() => {
-		if (taskId && isEnterPressed) {
+		if (taskId && isEnterPressed && !isStarred) {
 			onDelete()
 		}
-	}, [taskId, isEnterPressed, onDelete])
+	}, [taskId, isEnterPressed, isStarred, onDelete])
 
 	return (
 		<AlertDialog {...props}>
 			<AlertDialogContent onEscapeKeyDown={() => onOpenChange?.(false)}>
 				<AlertDialogHeader>
-					<AlertDialogTitle>{t("history:deleteTask")}</AlertDialogTitle>
-					<AlertDialogDescription>{t("history:deleteTaskMessage")}</AlertDialogDescription>
+					<AlertDialogTitle>
+						{isStarred ? t("history:deleteStarredTask") : t("history:deleteTask")}
+					</AlertDialogTitle>
+					<AlertDialogDescription>
+						{isStarred ? t("history:deleteStarredTaskMessage") : t("history:deleteTaskMessage")}
+					</AlertDialogDescription>
 				</AlertDialogHeader>
 				<AlertDialogFooter>
 					<AlertDialogCancel asChild>
 						<Button variant="secondary">{t("history:cancel")}</Button>
 					</AlertDialogCancel>
-					<AlertDialogAction asChild>
-						<Button variant="destructive" onClick={onDelete}>
-							{t("history:delete")}
-						</Button>
-					</AlertDialogAction>
+					{!isStarred && (
+						<AlertDialogAction asChild>
+							<Button variant="destructive" onClick={onDelete}>
+								{t("history:delete")}
+							</Button>
+						</AlertDialogAction>
+					)}
 				</AlertDialogFooter>
 			</AlertDialogContent>
 		</AlertDialog>
diff --git a/webview-ui/src/components/history/StarButton.tsx b/webview-ui/src/components/history/StarButton.tsx
new file mode 100644
index 00000000000..016cdd7ff2f
--- /dev/null
+++ b/webview-ui/src/components/history/StarButton.tsx
@@ -0,0 +1,40 @@
+import React from "react"
+import { cn } from "@/lib/utils"
+import { StandardTooltip } from "@/components/ui"
+import { useAppTranslation } from "@/i18n/TranslationContext"
+
+interface StarButtonProps {
+	itemId: string
+	isStarred?: boolean
+	onToggleStar: (itemId: string) => void
+	className?: string
+}
+
+export const StarButton: React.FC<StarButtonProps> = ({ itemId, isStarred, onToggleStar, className }) => {
+	const { t } = useAppTranslation()
+
+	const handleClick = (e: React.MouseEvent) => {
+		e.stopPropagation()
+		onToggleStar(itemId)
+	}
+
+	return (
+		<StandardTooltip content={isStarred ? t("history:unstarTask") : t("history:starTask")}>
+			<button
+				onClick={handleClick}
+				className={cn(
+					"p-1 rounded hover:bg-vscode-toolbar-hoverBackground transition-colors",
+					"focus:outline-none focus:ring-1 focus:ring-vscode-focusBorder",
+					className,
+				)}
+				aria-label={isStarred ? t("history:unstarTask") : t("history:starTask")}>
+				<span
+					className={cn("codicon", {
+						"codicon-star-full text-vscode-notificationsWarningIcon-foreground": isStarred,
+						"codicon-star-empty": !isStarred,
+					})}
+				/>
+			</button>
+		</StandardTooltip>
+	)
+}
diff --git a/webview-ui/src/components/history/TaskItemHeader.tsx b/webview-ui/src/components/history/TaskItemHeader.tsx
index bdddb090c86..f3bed921bd9 100644
--- a/webview-ui/src/components/history/TaskItemHeader.tsx
+++ b/webview-ui/src/components/history/TaskItemHeader.tsx
@@ -2,7 +2,9 @@ import React from "react"
 import type { HistoryItem } from "@roo-code/types"
 import { formatDate } from "@/utils/format"
 import { DeleteButton } from "./DeleteButton"
+import { StarButton } from "./StarButton"
 import { cn } from "@/lib/utils"
+import { vscode } from "@/utils/vscode"
 
 export interface TaskItemHeaderProps {
 	item: HistoryItem
@@ -11,12 +13,16 @@ export interface TaskItemHeaderProps {
 }
 
 const TaskItemHeader: React.FC<TaskItemHeaderProps> = ({ item, isSelectionMode, onDelete }) => {
+	const handleToggleStar = (itemId: string) => {
+		vscode.postMessage({ type: "toggleTaskStar", text: itemId })
+	}
+
 	return (
 		<div
 			className={cn("flex justify-between items-center", {
 				// this is to balance out the margin when we don't have a delete button
 				// because the delete button sorta pushes the date up due to its size
-				"mb-1": !onDelete,
+				"mb-1": !onDelete && !item.starred,
 			})}>
 			<div className="flex items-center flex-wrap gap-x-2 text-xs">
 				<span className="text-vscode-descriptionForeground font-medium text-sm uppercase">
@@ -27,6 +33,7 @@ const TaskItemHeader: React.FC<TaskItemHeaderProps> = ({ item, isSelectionMode,
 			{/* Action Buttons */}
 			{!isSelectionMode && (
 				<div className="flex flex-row gap-0 items-center opacity-20 group-hover:opacity-50 hover:opacity-100">
+					<StarButton itemId={item.id} isStarred={item.starred} onToggleStar={handleToggleStar} />
 					{onDelete && <DeleteButton itemId={item.id} onDelete={onDelete} />}
 				</div>
 			)}
diff --git a/webview-ui/src/components/history/useTaskSearch.ts b/webview-ui/src/components/history/useTaskSearch.ts
index 3969985b98a..8819197dea4 100644
--- a/webview-ui/src/components/history/useTaskSearch.ts
+++ b/webview-ui/src/components/history/useTaskSearch.ts
@@ -59,6 +59,11 @@ export const useTaskSearch = () => {
 
 		// Then sort the results
 		return [...results].sort((a, b) => {
+			// Always sort starred items to the top
+			if (a.starred && !b.starred) return -1
+			if (!a.starred && b.starred) return 1
+
+			// If both are starred or both are not starred, apply the selected sort
 			switch (sortOption) {
 				case "oldest":
 					return (a.ts || 0) - (b.ts || 0)
diff --git a/webview-ui/src/i18n/locales/en/history.json b/webview-ui/src/i18n/locales/en/history.json
index 8d004331709..db38fee557e 100644
--- a/webview-ui/src/i18n/locales/en/history.json
+++ b/webview-ui/src/i18n/locales/en/history.json
@@ -15,6 +15,11 @@
 	"exportTask": "Export Task",
 	"deleteTask": "Delete Task",
 	"deleteTaskMessage": "Are you sure you want to delete this task? This action cannot be undone.",
+	"deleteStarredTask": "Cannot Delete Starred Task",
+	"deleteStarredTaskMessage": "This task is starred and cannot be deleted. Please unstar it first if you want to delete it.",
+	"starTask": "Star task",
+	"unstarTask": "Unstar task",
+	"starredTasksExcluded": "{{count}} starred task(s) will not be deleted",
 	"cancel": "Cancel",
 	"delete": "Delete",
 	"exitSelection": "Exit Selection",