diff --git a/src/core/webview/ClineProvider.ts b/src/core/webview/ClineProvider.ts
index 2353dff490c..2795630c313 100644
--- a/src/core/webview/ClineProvider.ts
+++ b/src/core/webview/ClineProvider.ts
@@ -1250,6 +1250,8 @@ export class ClineProvider extends EventEmitter<ClineProviderEvents> implements
 		const machineId = vscode.env.machineId
 		const allowedCommands = vscode.workspace.getConfiguration("roo-cline").get<string[]>("allowedCommands") || []
 		const cwd = this.cwd
+		const workspaceTrustEnabled =
+			vscode.workspace.getConfiguration("security").get<boolean>("workspace.trust.enabled") ?? false
 
 		return {
 			version: this.context.extension?.packageJSON?.version ?? "",
@@ -1325,6 +1327,7 @@ export class ClineProvider extends EventEmitter<ClineProviderEvents> implements
 			maxReadFileLine: maxReadFileLine ?? 500,
 			settingsImportedAt: this.settingsImportedAt,
 			showGreeting: showGreeting ?? true, // Ensure showGreeting is included in the returned state
+			workspaceTrustEnabled, // Add the workspace trust setting here
 		}
 	}
 
diff --git a/src/shared/ExtensionMessage.ts b/src/shared/ExtensionMessage.ts
index 822e4239b57..32e89779adf 100644
--- a/src/shared/ExtensionMessage.ts
+++ b/src/shared/ExtensionMessage.ts
@@ -209,6 +209,7 @@ export type ExtensionState = Pick<
 
 	renderContext: "sidebar" | "editor"
 	settingsImportedAt?: number
+	workspaceTrustEnabled?: boolean
 }
 
 export type { ClineMessage, ClineAsk, ClineSay }
diff --git a/webview-ui/src/components/history/HistoryPreview.tsx b/webview-ui/src/components/history/HistoryPreview.tsx
index 0bc4fb69a5f..1475eb4284a 100644
--- a/webview-ui/src/components/history/HistoryPreview.tsx
+++ b/webview-ui/src/components/history/HistoryPreview.tsx
@@ -1,8 +1,9 @@
-import { memo } from "react"
+import { memo, useEffect } from "react"
 
 import { vscode } from "@/utils/vscode"
 import { formatLargeNumber, formatDate } from "@/utils/format"
 import { Button, Checkbox } from "@/components/ui"
+import { useExtensionState } from "@/context/ExtensionStateContext" // Import the context hook
 
 import { useAppTranslation } from "../../i18n/TranslationContext"
 import { CopyButton } from "./CopyButton"
@@ -13,8 +14,15 @@ type HistoryPreviewProps = {
 }
 const HistoryPreview = ({ showHistoryView }: HistoryPreviewProps) => {
 	const { tasks, showAllWorkspaces, setShowAllWorkspaces } = useTaskSearch()
+	const { workspaceTrustEnabled } = useExtensionState()
 	const { t } = useAppTranslation()
 
+	useEffect(() => {
+		if (!workspaceTrustEnabled) {
+			setShowAllWorkspaces(true)
+		}
+	}, [workspaceTrustEnabled, setShowAllWorkspaces])
+
 	return (
 		<div className="flex flex-col gap-3 shrink-0 mx-5">
 			<div className="flex items-center justify-between text-vscode-descriptionForeground">
@@ -26,17 +34,19 @@ const HistoryPreview = ({ showHistoryView }: HistoryPreviewProps) => {
 					{t("history:viewAll")}
 				</Button>
 			</div>
-			<div className="flex items-center gap-2 mb-2">
-				<Checkbox
-					id="show-all-workspaces"
-					checked={showAllWorkspaces}
-					onCheckedChange={(checked) => setShowAllWorkspaces(checked === true)}
-					variant="description"
-				/>
-				<label htmlFor="show-all-workspaces" className="text-xs text-vscode-foreground cursor-pointer">
-					{t("history:showAllWorkspaces")}
-				</label>
-			</div>
+			{workspaceTrustEnabled && (
+				<div className="flex items-center gap-2 mb-2">
+					<Checkbox
+						id="show-all-workspaces"
+						checked={showAllWorkspaces}
+						onCheckedChange={(checked) => setShowAllWorkspaces(checked === true)}
+						variant="description"
+					/>
+					<label htmlFor="show-all-workspaces" className="text-xs text-vscode-foreground cursor-pointer">
+						{t("history:showAllWorkspaces")}
+					</label>
+				</div>
+			)}
 			{tasks.slice(0, 3).map((item) => (
 				<div
 					key={item.id}
@@ -85,7 +95,7 @@ const HistoryPreview = ({ showHistoryView }: HistoryPreviewProps) => {
 								</>
 							)}
 						</div>
-						{showAllWorkspaces && item.workspace && (
+						{showAllWorkspaces && workspaceTrustEnabled && item.workspace && (
 							<div className="flex flex-row gap-1 text-vscode-descriptionForeground text-xs mt-1">
 								<span className="codicon codicon-folder scale-80" />
 								<span>{item.workspace}</span>
diff --git a/webview-ui/src/components/history/HistoryView.tsx b/webview-ui/src/components/history/HistoryView.tsx
index 2c244e21cd0..5ef675061ce 100644
--- a/webview-ui/src/components/history/HistoryView.tsx
+++ b/webview-ui/src/components/history/HistoryView.tsx
@@ -1,4 +1,4 @@
-import React, { memo, useState } from "react"
+import React, { memo, useState, useEffect } from "react"
 import { DeleteTaskDialog } from "./DeleteTaskDialog"
 import { BatchDeleteTaskDialog } from "./BatchDeleteTaskDialog"
 import prettyBytes from "pretty-bytes"
@@ -11,6 +11,7 @@ import { formatLargeNumber, formatDate } from "@/utils/format"
 import { cn } from "@/lib/utils"
 import { Button, Checkbox } from "@/components/ui"
 import { useAppTranslation } from "@/i18n/TranslationContext"
+import { useExtensionState } from "@/context/ExtensionStateContext" // Import the context hook
 
 import { Tab, TabContent, TabHeader } from "../common/Tab"
 import { useTaskSearch } from "./useTaskSearch"
@@ -35,12 +36,19 @@ const HistoryView = ({ onDone }: HistoryViewProps) => {
 		setShowAllWorkspaces,
 	} = useTaskSearch()
 	const { t } = useAppTranslation()
+	const { workspaceTrustEnabled } = useExtensionState()
 
 	const [deleteTaskId, setDeleteTaskId] = useState<string | null>(null)
 	const [isSelectionMode, setIsSelectionMode] = useState(false)
 	const [selectedTaskIds, setSelectedTaskIds] = useState<string[]>([])
 	const [showBatchDeleteDialog, setShowBatchDeleteDialog] = useState<boolean>(false)
 
+	useEffect(() => {
+		if (!workspaceTrustEnabled) {
+			setShowAllWorkspaces(true)
+		}
+	}, [workspaceTrustEnabled, setShowAllWorkspaces])
+
 	// Toggle selection mode
 	const toggleSelectionMode = () => {
 		setIsSelectionMode(!isSelectionMode)
@@ -156,17 +164,19 @@ const HistoryView = ({ onDone }: HistoryViewProps) => {
 						</VSCodeRadio>
 					</VSCodeRadioGroup>
 
-					<div className="flex items-center gap-2">
-						<Checkbox
-							id="show-all-workspaces-view"
-							checked={showAllWorkspaces}
-							onCheckedChange={(checked) => setShowAllWorkspaces(checked === true)}
-							variant="description"
-						/>
-						<label htmlFor="show-all-workspaces-view" className="text-vscode-foreground cursor-pointer">
-							{t("history:showAllWorkspaces")}
-						</label>
-					</div>
+					{workspaceTrustEnabled && (
+						<div className="flex items-center gap-2">
+							<Checkbox
+								id="show-all-workspaces-view"
+								checked={showAllWorkspaces}
+								onCheckedChange={(checked) => setShowAllWorkspaces(checked === true)}
+								variant="description"
+							/>
+							<label htmlFor="show-all-workspaces-view" className="text-vscode-foreground cursor-pointer">
+								{t("history:showAllWorkspaces")}
+							</label>
+						</div>
+					)}
 
 					{/* Select all control in selection mode */}
 					{isSelectionMode && tasks.length > 0 && (
@@ -436,7 +446,7 @@ const HistoryView = ({ onDone }: HistoryViewProps) => {
 											</div>
 										)}
 
-										{showAllWorkspaces && item.workspace && (
+										{showAllWorkspaces && workspaceTrustEnabled && item.workspace && (
 											<div className="flex flex-row gap-1 text-vscode-descriptionForeground text-xs">
 												<span className="codicon codicon-folder scale-80" />
 												<span>{item.workspace}</span>
diff --git a/webview-ui/src/context/ExtensionStateContext.tsx b/webview-ui/src/context/ExtensionStateContext.tsx
index 8b50bf0aca7..9392b77efe9 100644
--- a/webview-ui/src/context/ExtensionStateContext.tsx
+++ b/webview-ui/src/context/ExtensionStateContext.tsx
@@ -87,6 +87,7 @@ export interface ExtensionStateContextType extends ExtensionState {
 	setPinnedApiConfigs: (value: Record<string, boolean>) => void
 	togglePinnedApiConfig: (configName: string) => void
 	setShowGreeting: (value: boolean) => void
+	workspaceTrustEnabled: boolean
 }
 
 export const ExtensionStateContext = createContext<ExtensionStateContextType | undefined>(undefined)
@@ -165,6 +166,7 @@ export const ExtensionStateContextProvider: React.FC<{ children: React.ReactNode
 		terminalZshOhMy: false, // Default Oh My Zsh integration setting
 		terminalZshP10k: false, // Default Powerlevel10k integration setting
 		terminalZdotdir: false, // Default ZDOTDIR handling setting
+		workspaceTrustEnabled: false, // Add default value for the new property
 	})
 
 	const [didHydrateState, setDidHydrateState] = useState(false)
@@ -243,6 +245,7 @@ export const ExtensionStateContextProvider: React.FC<{ children: React.ReactNode
 
 	const contextValue: ExtensionStateContextType = {
 		...state,
+		workspaceTrustEnabled: state.workspaceTrustEnabled ?? false,
 		didHydrateState,
 		showWelcome,
 		theme,