diff --git a/src/__tests__/extension.spec.ts b/src/__tests__/extension.spec.ts
index 1803eb4d36..31e72e6648 100644
--- a/src/__tests__/extension.spec.ts
+++ b/src/__tests__/extension.spec.ts
@@ -162,6 +162,7 @@ vi.mock("../utils/autoImportSettings", () => ({
 // Avoid filesystem access during activation by stubbing background purge
 vi.mock("../utils/task-history-retention", () => ({
 	startBackgroundRetentionPurge: vi.fn(),
+	startBackgroundCheckpointPurge: vi.fn(),
 }))
 
 // Ensure storage base path resolves to provided path to avoid touching VS Code config
diff --git a/webview-ui/src/components/history/HistoryView.tsx b/webview-ui/src/components/history/HistoryView.tsx
index 88b6551881..fb621f5ec0 100644
--- a/webview-ui/src/components/history/HistoryView.tsx
+++ b/webview-ui/src/components/history/HistoryView.tsx
@@ -1,14 +1,21 @@
 import React, { memo, useState, useMemo } from "react"
-import { ArrowLeft } from "lucide-react"
+import { ArrowLeft, Settings } from "lucide-react"
 import { DeleteTaskDialog } from "./DeleteTaskDialog"
 import { BatchDeleteTaskDialog } from "./BatchDeleteTaskDialog"
 import { Virtuoso } from "react-virtuoso"
 
+import { TASK_HISTORY_RETENTION_OPTIONS, type TaskHistoryRetentionSetting } from "@roo-code/types"
+
 import { VSCodeTextField } from "@vscode/webview-ui-toolkit/react"
 
+import { vscode } from "@/utils/vscode"
+import { useExtensionState } from "@/context/ExtensionStateContext"
 import {
 	Button,
 	Checkbox,
+	Popover,
+	PopoverContent,
+	PopoverTrigger,
 	Select,
 	SelectContent,
 	SelectItem,
@@ -41,6 +48,7 @@ const HistoryView = ({ onDone }: HistoryViewProps) => {
 		showAllWorkspaces,
 		setShowAllWorkspaces,
 	} = useTaskSearch()
+	const { taskHistoryRetention } = useExtensionState()
 	const { t } = useAppTranslation()
 
 	// Use grouped tasks hook
@@ -51,6 +59,19 @@ const HistoryView = ({ onDone }: HistoryViewProps) => {
 	const [isSelectionMode, setIsSelectionMode] = useState(false)
 	const [selectedTaskIds, setSelectedTaskIds] = useState<string[]>([])
 	const [showBatchDeleteDialog, setShowBatchDeleteDialog] = useState<boolean>(false)
+	const [isRetentionPopoverOpen, setIsRetentionPopoverOpen] = useState(false)
+
+	// Normalize retention setting to ensure it's valid
+	const normalizedRetention: TaskHistoryRetentionSetting = TASK_HISTORY_RETENTION_OPTIONS.includes(
+		taskHistoryRetention as TaskHistoryRetentionSetting,
+	)
+		? (taskHistoryRetention as TaskHistoryRetentionSetting)
+		: "never"
+
+	// Handle retention setting change
+	const handleRetentionChange = (value: TaskHistoryRetentionSetting) => {
+		vscode.postMessage({ type: "updateSettings", updatedSettings: { taskHistoryRetention: value } })
+	}
 
 	// Get subtask count for a task
 	const getSubtaskCount = useMemo(() => {
@@ -116,20 +137,67 @@ const HistoryView = ({ onDone }: HistoryViewProps) => {
 						</Button>
 						<h3 className="text-vscode-foreground m-0">{t("history:history")}</h3>
 					</div>
-					<StandardTooltip
-						content={
-							isSelectionMode ? `${t("history:exitSelectionMode")}` : `${t("history:enterSelectionMode")}`
-						}>
-						<Button
-							variant={isSelectionMode ? "primary" : "secondary"}
-							onClick={toggleSelectionMode}
-							data-testid="toggle-selection-mode-button">
-							<span
-								className={`codicon ${isSelectionMode ? "codicon-check-all" : "codicon-checklist"} mr-1`}
-							/>
-							{isSelectionMode ? t("history:exitSelection") : t("history:selectionMode")}
-						</Button>
-					</StandardTooltip>
+					<div className="flex items-center gap-2">
+						<Popover open={isRetentionPopoverOpen} onOpenChange={setIsRetentionPopoverOpen}>
+							<StandardTooltip content={t("settings:aboutRetention.label")}>
+								<PopoverTrigger asChild>
+									<Button variant="ghost" size="icon" data-testid="history-retention-settings-button">
+										<Settings className="size-4" />
+									</Button>
+								</PopoverTrigger>
+							</StandardTooltip>
+							<PopoverContent className="w-72" align="end">
+								<div className="space-y-3">
+									<h4 className="font-medium text-sm">{t("settings:aboutRetention.label")}</h4>
+									<Select
+										value={normalizedRetention}
+										onValueChange={(value: TaskHistoryRetentionSetting) => {
+											handleRetentionChange(value)
+										}}>
+										<SelectTrigger className="w-full">
+											<SelectValue placeholder={t("settings:common.select")} />
+										</SelectTrigger>
+										<SelectContent>
+											<SelectItem value="never">
+												{t("settings:aboutRetention.options.never")}
+											</SelectItem>
+											<SelectItem value="90">
+												{t("settings:aboutRetention.options.90")}
+											</SelectItem>
+											<SelectItem value="60">
+												{t("settings:aboutRetention.options.60")}
+											</SelectItem>
+											<SelectItem value="30">
+												{t("settings:aboutRetention.options.30")}
+											</SelectItem>
+											<SelectItem value="7">{t("settings:aboutRetention.options.7")}</SelectItem>
+											<SelectItem value="3">{t("settings:aboutRetention.options.3")}</SelectItem>
+										</SelectContent>
+									</Select>
+									<p className="text-vscode-descriptionForeground text-xs">
+										{t("settings:aboutRetention.description")}
+									</p>
+									<p className="text-red-500 text-xs">{t("settings:aboutRetention.warning")}</p>
+								</div>
+							</PopoverContent>
+						</Popover>
+						<StandardTooltip
+							content={
+								isSelectionMode
+									? `${t("history:exitSelectionMode")}`
+									: `${t("history:enterSelectionMode")}`
+							}>
+							<Button
+								variant={isSelectionMode ? "primary" : "secondary"}
+								onClick={toggleSelectionMode}
+								data-testid="toggle-selection-mode-button">
+								<span
+									className={`codicon ${isSelectionMode ? "codicon-check-all" : "codicon-checklist"} mr-1`}
+								/>
+								{isSelectionMode ? t("history:exitSelection") : t("history:selectionMode")}
+							</Button>
+						</StandardTooltip>
+					</div>
 				</div>
 				<div className="flex flex-col gap-2">
 					<VSCodeTextField
diff --git a/webview-ui/src/components/settings/About.tsx b/webview-ui/src/components/settings/About.tsx
index f85582fc33..c5345f8da1 100644
--- a/webview-ui/src/components/settings/About.tsx
+++ b/webview-ui/src/components/settings/About.tsx
@@ -16,13 +16,13 @@ import {
 } from "lucide-react"
 import { VSCodeCheckbox, VSCodeLink } from "@vscode/webview-ui-toolkit/react"
 
-import type { TelemetrySetting, TaskHistoryRetentionSetting } from "@roo-code/types"
+import type { TelemetrySetting } from "@roo-code/types"
 
 import { Package } from "@roo/package"
 
 import { vscode } from "@/utils/vscode"
 import { cn } from "@/lib/utils"
-import { Button, Select, SelectContent, SelectItem, SelectTrigger, SelectValue } from "@/components/ui"
+import { Button } from "@/components/ui"
 
 import { SectionHeader } from "./SectionHeader"
 import { Section } from "./Section"
@@ -37,8 +37,6 @@ type AboutProps = HTMLAttributes<HTMLDivElement> & {
 	setTelemetrySetting: (setting: TelemetrySetting) => void
 	debug?: boolean
 	setDebug?: (debug: boolean) => void
-	taskHistoryRetention: TaskHistoryRetentionSetting
-	setTaskHistoryRetention: (value: TaskHistoryRetentionSetting) => void
 	taskHistorySize?: TaskHistorySize
 }
 
@@ -47,8 +45,6 @@ export const About = ({
 	setTelemetrySetting,
 	debug,
 	setDebug,
-	taskHistoryRetention,
-	setTaskHistoryRetention,
 	taskHistorySize,
 	className,
 	...props
@@ -195,37 +191,6 @@ export const About = ({
 			</Section>
 
 			<Section className="space-y-0">
-				<SearchableSetting
-					settingId="about-task-history-retention"
-					section="about"
-					label={t("settings:aboutRetention.label")}
-					className="mt-4">
-					<h3>{t("settings:aboutRetention.label")}</h3>
-					<div className="mt-2">
-						<Select
-							value={taskHistoryRetention}
-							onValueChange={(value: TaskHistoryRetentionSetting) => {
-								setTaskHistoryRetention(value)
-							}}>
-							<SelectTrigger className="w-64">
-								<SelectValue placeholder={t("settings:common.select")} />
-							</SelectTrigger>
-							<SelectContent>
-								<SelectItem value="never">{t("settings:aboutRetention.options.never")}</SelectItem>
-								<SelectItem value="90">{t("settings:aboutRetention.options.90")}</SelectItem>
-								<SelectItem value="60">{t("settings:aboutRetention.options.60")}</SelectItem>
-								<SelectItem value="30">{t("settings:aboutRetention.options.30")}</SelectItem>
-								<SelectItem value="7">{t("settings:aboutRetention.options.7")}</SelectItem>
-								<SelectItem value="3">{t("settings:aboutRetention.options.3")}</SelectItem>
-							</SelectContent>
-						</Select>
-						<div className="text-vscode-descriptionForeground text-sm mt-1">
-							{t("settings:aboutRetention.description")}
-						</div>
-						<div className="text-red-500 text-sm mt-1">{t("settings:aboutRetention.warning")}</div>
-					</div>
-				</SearchableSetting>
-
 				<SearchableSetting
 					settingId="about-task-history-count"
 					section="about"
diff --git a/webview-ui/src/components/settings/SettingsView.tsx b/webview-ui/src/components/settings/SettingsView.tsx
index 7342351614..c235149356 100644
--- a/webview-ui/src/components/settings/SettingsView.tsx
+++ b/webview-ui/src/components/settings/SettingsView.tsx
@@ -974,8 +974,6 @@ const SettingsView = forwardRef<SettingsViewRef, SettingsViewProps>(({ onDone, t
 								setTelemetrySetting={setTelemetrySetting}
 								debug={cachedState.debug}
 								setDebug={setDebug}
-								taskHistoryRetention={normalizedTaskHistoryRetention}
-								setTaskHistoryRetention={(value) => setCachedStateField("taskHistoryRetention", value)}
 								taskHistorySize={taskHistorySize}
 							/>
 						)}
diff --git a/webview-ui/src/components/settings/__tests__/About.spec.tsx b/webview-ui/src/components/settings/__tests__/About.spec.tsx
index 92791b4ac5..b62b7c1358 100644
--- a/webview-ui/src/components/settings/__tests__/About.spec.tsx
+++ b/webview-ui/src/components/settings/__tests__/About.spec.tsx
@@ -31,8 +31,6 @@ describe("About", () => {
 	const defaultProps: ComponentProps<typeof About> = {
 		telemetrySetting: "enabled" as const,
 		setTelemetrySetting: vi.fn(),
-		taskHistoryRetention: "never",
-		setTaskHistoryRetention: vi.fn(),
 	}
 
 	beforeEach(() => {