diff --git a/packages/types/src/global-settings.ts b/packages/types/src/global-settings.ts
index dc5a9e6744..8d17bf6773 100644
--- a/packages/types/src/global-settings.ts
+++ b/packages/types/src/global-settings.ts
@@ -37,6 +37,7 @@ export const globalSettingsSchema = z.object({
 	currentApiConfigName: z.string().optional(),
 	listApiConfigMeta: z.array(providerSettingsEntrySchema).optional(),
 	pinnedApiConfigs: z.record(z.string(), z.boolean()).optional(),
+	pinnedTasks: z.record(z.string(), z.boolean()).optional(),
 
 	lastShownAnnouncementId: z.string().optional(),
 	customInstructions: z.string().optional(),
@@ -218,6 +219,7 @@ export const EVALS_SETTINGS: RooCodeSettings = {
 	lastShownAnnouncementId: "jul-09-2025-3-23-0",
 
 	pinnedApiConfigs: {},
+	pinnedTasks: {},
 
 	autoApprovalEnabled: true,
 	alwaysAllowReadOnly: true,
diff --git a/src/core/webview/ClineProvider.ts b/src/core/webview/ClineProvider.ts
index a0739052b2..66a8351b6e 100644
--- a/src/core/webview/ClineProvider.ts
+++ b/src/core/webview/ClineProvider.ts
@@ -1479,6 +1479,7 @@ export class ClineProvider
 			currentApiConfigName,
 			listApiConfigMeta,
 			pinnedApiConfigs,
+			pinnedTasks,
 			mode,
 			customModePrompts,
 			customSupportPrompts,
@@ -1583,6 +1584,7 @@ export class ClineProvider
 			currentApiConfigName: currentApiConfigName ?? "default",
 			listApiConfigMeta: listApiConfigMeta ?? [],
 			pinnedApiConfigs: pinnedApiConfigs ?? {},
+			pinnedTasks: pinnedTasks ?? {},
 			mode: mode ?? defaultModeSlug,
 			customModePrompts: customModePrompts ?? {},
 			customSupportPrompts: customSupportPrompts ?? {},
@@ -1760,6 +1762,7 @@ export class ClineProvider
 			currentApiConfigName: stateValues.currentApiConfigName ?? "default",
 			listApiConfigMeta: stateValues.listApiConfigMeta ?? [],
 			pinnedApiConfigs: stateValues.pinnedApiConfigs ?? {},
+			pinnedTasks: stateValues.pinnedTasks ?? {},
 			modeApiConfigs: stateValues.modeApiConfigs ?? ({} as Record<Mode, string>),
 			customModePrompts: stateValues.customModePrompts ?? {},
 			customSupportPrompts: stateValues.customSupportPrompts ?? {},
diff --git a/src/core/webview/webviewMessageHandler.ts b/src/core/webview/webviewMessageHandler.ts
index 763e118125..d573058bce 100644
--- a/src/core/webview/webviewMessageHandler.ts
+++ b/src/core/webview/webviewMessageHandler.ts
@@ -1307,6 +1307,21 @@ export const webviewMessageHandler = async (
 				await provider.postStateToWebview()
 			}
 			break
+		case "toggleTaskPin":
+			if (message.text) {
+				const currentPinnedTasks = getGlobalState("pinnedTasks") ?? {}
+				const updatedPinnedTasks: Record<string, boolean> = { ...currentPinnedTasks }
+
+				if (currentPinnedTasks[message.text]) {
+					delete updatedPinnedTasks[message.text]
+				} else {
+					updatedPinnedTasks[message.text] = true
+				}
+
+				await updateGlobalState("pinnedTasks", updatedPinnedTasks)
+				await provider.postStateToWebview()
+			}
+			break
 		case "enhancementApiConfigId":
 			await updateGlobalState("enhancementApiConfigId", message.text)
 			await provider.postStateToWebview()
diff --git a/src/shared/ExtensionMessage.ts b/src/shared/ExtensionMessage.ts
index 5320190a7b..b14e38847a 100644
--- a/src/shared/ExtensionMessage.ts
+++ b/src/shared/ExtensionMessage.ts
@@ -99,6 +99,7 @@ export interface ExtensionMessage {
 		| "maxReadFileLine"
 		| "fileSearchResults"
 		| "toggleApiConfigPin"
+		| "toggleTaskPin"
 		| "acceptInput"
 		| "setHistoryPreviewCollapsed"
 		| "commandExecutionStatus"
@@ -199,6 +200,7 @@ export type ExtensionState = Pick<
 	| "currentApiConfigName"
 	| "listApiConfigMeta"
 	| "pinnedApiConfigs"
+	| "pinnedTasks"
 	// | "lastShownAnnouncementId"
 	| "customInstructions"
 	// | "taskHistory" // Optional in GlobalSettings, required here.
diff --git a/src/shared/WebviewMessage.ts b/src/shared/WebviewMessage.ts
index a91d1af7ba..467ab7d649 100644
--- a/src/shared/WebviewMessage.ts
+++ b/src/shared/WebviewMessage.ts
@@ -169,6 +169,7 @@ export interface WebviewMessage {
 		| "maxDiagnosticMessages"
 		| "searchFiles"
 		| "toggleApiConfigPin"
+		| "toggleTaskPin"
 		| "setHistoryPreviewCollapsed"
 		| "hasOpenedModeSelector"
 		| "accountButtonClicked"
diff --git a/webview-ui/src/components/history/DeleteButton.tsx b/webview-ui/src/components/history/DeleteButton.tsx
index 3e99027546..4317c2426d 100644
--- a/webview-ui/src/components/history/DeleteButton.tsx
+++ b/webview-ui/src/components/history/DeleteButton.tsx
@@ -2,6 +2,7 @@ import { useCallback } from "react"
 
 import { Button, StandardTooltip } from "@/components/ui"
 import { useAppTranslation } from "@/i18n/TranslationContext"
+import { useExtensionState } from "@/context/ExtensionStateContext"
 import { vscode } from "@/utils/vscode"
 
 type DeleteButtonProps = {
@@ -11,17 +12,27 @@ type DeleteButtonProps = {
 
 export const DeleteButton = ({ itemId, onDelete }: DeleteButtonProps) => {
 	const { t } = useAppTranslation()
+	const { pinnedTasks } = useExtensionState()
+	const isPinned = pinnedTasks?.[itemId] || false
 
 	const handleDeleteClick = useCallback(
 		(e: React.MouseEvent) => {
 			e.stopPropagation()
+
+			// Prevent deletion of pinned tasks
+			if (isPinned) {
+				// Show a simple alert for now - we can improve this later
+				alert(t("history:pinnedTaskCannotDelete"))
+				return
+			}
+
 			if (e.shiftKey) {
 				vscode.postMessage({ type: "deleteTaskWithId", text: itemId })
 			} else if (onDelete) {
 				onDelete(itemId)
 			}
 		},
-		[itemId, onDelete],
+		[itemId, onDelete, isPinned, t],
 	)
 
 	return (
diff --git a/webview-ui/src/components/history/TaskItemHeader.tsx b/webview-ui/src/components/history/TaskItemHeader.tsx
index bdddb090c8..68a0ade330 100644
--- a/webview-ui/src/components/history/TaskItemHeader.tsx
+++ b/webview-ui/src/components/history/TaskItemHeader.tsx
@@ -3,6 +3,11 @@ import type { HistoryItem } from "@roo-code/types"
 import { formatDate } from "@/utils/format"
 import { DeleteButton } from "./DeleteButton"
 import { cn } from "@/lib/utils"
+import { Button } from "@/components/ui/button"
+import { StandardTooltip } from "@/components/ui"
+import { useExtensionState } from "@/context/ExtensionStateContext"
+import { vscode } from "@/utils/vscode"
+import { useAppTranslation } from "@/i18n/TranslationContext"
 
 export interface TaskItemHeaderProps {
 	item: HistoryItem
@@ -11,6 +16,18 @@ export interface TaskItemHeaderProps {
 }
 
 const TaskItemHeader: React.FC<TaskItemHeaderProps> = ({ item, isSelectionMode, onDelete }) => {
+	const { pinnedTasks, togglePinnedTask } = useExtensionState()
+	const { t } = useAppTranslation()
+	const isPinned = pinnedTasks?.[item.id] || false
+
+	const handlePinToggle = (e: React.MouseEvent) => {
+		e.stopPropagation()
+		togglePinnedTask(item.id)
+		vscode.postMessage({
+			type: "toggleTaskPin",
+			text: item.id,
+		})
+	}
 	return (
 		<div
 			className={cn("flex justify-between items-center", {
@@ -27,6 +44,17 @@ 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">
+					<StandardTooltip content={isPinned ? t("history:unpin") : t("history:pin")}>
+						<Button
+							variant="ghost"
+							size="sm"
+							onClick={handlePinToggle}
+							className={cn("size-5 flex items-center justify-center", {
+								"opacity-100 bg-accent": isPinned,
+							})}>
+							<span className="codicon codicon-pin text-xs opacity-50" />
+						</Button>
+					</StandardTooltip>
 					{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 3969985b98..7674ce08b0 100644
--- a/webview-ui/src/components/history/useTaskSearch.ts
+++ b/webview-ui/src/components/history/useTaskSearch.ts
@@ -7,7 +7,7 @@ import { useExtensionState } from "@/context/ExtensionStateContext"
 type SortOption = "newest" | "oldest" | "mostExpensive" | "mostTokens" | "mostRelevant"
 
 export const useTaskSearch = () => {
-	const { taskHistory, cwd } = useExtensionState()
+	const { taskHistory, cwd, pinnedTasks } = useExtensionState()
 	const [searchQuery, setSearchQuery] = useState("")
 	const [sortOption, setSortOption] = useState<SortOption>("newest")
 	const [lastNonRelevantSort, setLastNonRelevantSort] = useState<SortOption | null>("newest")
@@ -57,8 +57,16 @@ export const useTaskSearch = () => {
 			})
 		}
 
-		// Then sort the results
+		// Then sort the results with pinned tasks first
 		return [...results].sort((a, b) => {
+			const aPinned = pinnedTasks?.[a.id] || false
+			const bPinned = pinnedTasks?.[b.id] || false
+
+			// Pinned tasks always come first
+			if (aPinned && !bPinned) return -1
+			if (!aPinned && bPinned) return 1
+
+			// If both are pinned or both are unpinned, sort by the selected option
 			switch (sortOption) {
 				case "oldest":
 					return (a.ts || 0) - (b.ts || 0)
@@ -76,7 +84,7 @@ export const useTaskSearch = () => {
 					return (b.ts || 0) - (a.ts || 0)
 			}
 		})
-	}, [presentableTasks, searchQuery, fzf, sortOption])
+	}, [presentableTasks, searchQuery, fzf, sortOption, pinnedTasks])
 
 	return {
 		tasks,
diff --git a/webview-ui/src/context/ExtensionStateContext.tsx b/webview-ui/src/context/ExtensionStateContext.tsx
index b156d0193b..719bee9e47 100644
--- a/webview-ui/src/context/ExtensionStateContext.tsx
+++ b/webview-ui/src/context/ExtensionStateContext.tsx
@@ -129,6 +129,9 @@ export interface ExtensionStateContextType extends ExtensionState {
 	pinnedApiConfigs?: Record<string, boolean>
 	setPinnedApiConfigs: (value: Record<string, boolean>) => void
 	togglePinnedApiConfig: (configName: string) => void
+	pinnedTasks?: Record<string, boolean>
+	setPinnedTasks: (value: Record<string, boolean>) => void
+	togglePinnedTask: (taskId: string) => void
 	terminalCompressProgressBar?: boolean
 	setTerminalCompressProgressBar: (value: boolean) => void
 	setHistoryPreviewCollapsed: (value: boolean) => void
@@ -216,6 +219,7 @@ export const ExtensionStateContextProvider: React.FC<{ children: React.ReactNode
 		maxImageFileSize: 5, // Default max image file size in MB
 		maxTotalImageSize: 20, // Default max total image size in MB
 		pinnedApiConfigs: {}, // Empty object for pinned API configs
+		pinnedTasks: {}, // Empty object for pinned tasks
 		terminalZshOhMy: false, // Default Oh My Zsh integration setting
 		maxConcurrentFileReads: 5, // Default concurrent file reads
 		terminalZshP10k: false, // Default Powerlevel10k integration setting
@@ -464,6 +468,7 @@ export const ExtensionStateContextProvider: React.FC<{ children: React.ReactNode
 		setMaxImageFileSize: (value) => setState((prevState) => ({ ...prevState, maxImageFileSize: value })),
 		setMaxTotalImageSize: (value) => setState((prevState) => ({ ...prevState, maxTotalImageSize: value })),
 		setPinnedApiConfigs: (value) => setState((prevState) => ({ ...prevState, pinnedApiConfigs: value })),
+		setPinnedTasks: (value) => setState((prevState) => ({ ...prevState, pinnedTasks: value })),
 		setTerminalCompressProgressBar: (value) =>
 			setState((prevState) => ({ ...prevState, terminalCompressProgressBar: value })),
 		togglePinnedApiConfig: (configId) =>
@@ -481,6 +486,21 @@ export const ExtensionStateContextProvider: React.FC<{ children: React.ReactNode
 
 				return { ...prevState, pinnedApiConfigs: newPinned }
 			}),
+		togglePinnedTask: (taskId) =>
+			setState((prevState) => {
+				const currentPinned = prevState.pinnedTasks || {}
+				const newPinned = {
+					...currentPinned,
+					[taskId]: !currentPinned[taskId],
+				}
+
+				// If the task is now unpinned, remove it from the object
+				if (!newPinned[taskId]) {
+					delete newPinned[taskId]
+				}
+
+				return { ...prevState, pinnedTasks: newPinned }
+			}),
 		setHistoryPreviewCollapsed: (value) =>
 			setState((prevState) => ({ ...prevState, historyPreviewCollapsed: value })),
 		setHasOpenedModeSelector: (value) => setState((prevState) => ({ ...prevState, hasOpenedModeSelector: value })),
diff --git a/webview-ui/src/i18n/locales/en/history.json b/webview-ui/src/i18n/locales/en/history.json
index 8d00433170..4f879ff07b 100644
--- a/webview-ui/src/i18n/locales/en/history.json
+++ b/webview-ui/src/i18n/locales/en/history.json
@@ -41,5 +41,8 @@
 		"mostTokens": "Most Tokens",
 		"mostRelevant": "Most Relevant"
 	},
-	"viewAllHistory": "View all tasks"
+	"viewAllHistory": "View all tasks",
+	"pin": "Pin task",
+	"unpin": "Unpin task",
+	"pinnedTaskCannotDelete": "Cannot delete pinned task. Unpin it first to delete."
 }