diff --git a/src/core/webview/ClineProvider.ts b/src/core/webview/ClineProvider.ts
index 87c92448e8..8c4a32c3c8 100644
--- a/src/core/webview/ClineProvider.ts
+++ b/src/core/webview/ClineProvider.ts
@@ -1873,7 +1873,7 @@ export class ClineProvider
 			followupAutoApproveTimeoutMs: followupAutoApproveTimeoutMs ?? 60000,
 			includeDiagnosticMessages: includeDiagnosticMessages ?? true,
 			maxDiagnosticMessages: maxDiagnosticMessages ?? 50,
-			includeTaskHistoryInEnhance: includeTaskHistoryInEnhance ?? false,
+			includeTaskHistoryInEnhance: includeTaskHistoryInEnhance ?? true,
 			remoteControlEnabled: remoteControlEnabled ?? false,
 		}
 	}
@@ -2061,7 +2061,7 @@ export class ClineProvider
 			includeDiagnosticMessages: stateValues.includeDiagnosticMessages ?? true,
 			maxDiagnosticMessages: stateValues.maxDiagnosticMessages ?? 50,
 			// Add includeTaskHistoryInEnhance setting
-			includeTaskHistoryInEnhance: stateValues.includeTaskHistoryInEnhance ?? false,
+			includeTaskHistoryInEnhance: stateValues.includeTaskHistoryInEnhance ?? true,
 			// Add remoteControlEnabled setting
 			remoteControlEnabled: stateValues.remoteControlEnabled ?? false,
 		}
diff --git a/src/core/webview/webviewMessageHandler.ts b/src/core/webview/webviewMessageHandler.ts
index d16ed06132..4dd0fee75e 100644
--- a/src/core/webview/webviewMessageHandler.ts
+++ b/src/core/webview/webviewMessageHandler.ts
@@ -1343,7 +1343,7 @@ export const webviewMessageHandler = async (
 			await provider.postStateToWebview()
 			break
 		case "includeTaskHistoryInEnhance":
-			await updateGlobalState("includeTaskHistoryInEnhance", message.bool ?? false)
+			await updateGlobalState("includeTaskHistoryInEnhance", message.bool ?? true)
 			await provider.postStateToWebview()
 			break
 		case "condensingApiConfigId":
diff --git a/webview-ui/src/components/settings/PromptsSettings.tsx b/webview-ui/src/components/settings/PromptsSettings.tsx
index ee112b54dd..d09b53fe47 100644
--- a/webview-ui/src/components/settings/PromptsSettings.tsx
+++ b/webview-ui/src/components/settings/PromptsSettings.tsx
@@ -46,7 +46,7 @@ const PromptsSettings = ({
 	} = useExtensionState()
 
 	// Use props if provided, otherwise fall back to context
-	const includeTaskHistoryInEnhance = propsIncludeTaskHistoryInEnhance ?? contextIncludeTaskHistoryInEnhance
+	const includeTaskHistoryInEnhance = propsIncludeTaskHistoryInEnhance ?? contextIncludeTaskHistoryInEnhance ?? true
 	const setIncludeTaskHistoryInEnhance = propsSetIncludeTaskHistoryInEnhance ?? contextSetIncludeTaskHistoryInEnhance
 
 	const [testPrompt, setTestPrompt] = useState("")
@@ -235,7 +235,7 @@ const PromptsSettings = ({
 								<>
 									<div>
 										<VSCodeCheckbox
-											checked={includeTaskHistoryInEnhance || false}
+											checked={includeTaskHistoryInEnhance}
 											onChange={(e: any) => {
 												const value = e.target.checked
 												setIncludeTaskHistoryInEnhance(value)
diff --git a/webview-ui/src/components/settings/SettingsView.tsx b/webview-ui/src/components/settings/SettingsView.tsx
index 9866c1e235..2738b82632 100644
--- a/webview-ui/src/components/settings/SettingsView.tsx
+++ b/webview-ui/src/components/settings/SettingsView.tsx
@@ -341,7 +341,7 @@ const SettingsView = forwardRef<SettingsViewRef, SettingsViewProps>(({ onDone, t
 			vscode.postMessage({ type: "condensingApiConfigId", text: condensingApiConfigId || "" })
 			vscode.postMessage({ type: "updateCondensingPrompt", text: customCondensingPrompt || "" })
 			vscode.postMessage({ type: "updateSupportPrompt", values: customSupportPrompts || {} })
-			vscode.postMessage({ type: "includeTaskHistoryInEnhance", bool: includeTaskHistoryInEnhance ?? false })
+			vscode.postMessage({ type: "includeTaskHistoryInEnhance", bool: includeTaskHistoryInEnhance ?? true })
 			vscode.postMessage({ type: "upsertApiConfiguration", text: currentApiConfigName, apiConfiguration })
 			vscode.postMessage({ type: "telemetrySetting", text: telemetrySetting })
 			vscode.postMessage({ type: "profileThresholds", values: profileThresholds })
diff --git a/webview-ui/src/context/ExtensionStateContext.tsx b/webview-ui/src/context/ExtensionStateContext.tsx
index ad35452079..b0045977c3 100644
--- a/webview-ui/src/context/ExtensionStateContext.tsx
+++ b/webview-ui/src/context/ExtensionStateContext.tsx
@@ -268,7 +268,7 @@ export const ExtensionStateContextProvider: React.FC<{ children: React.ReactNode
 		project: {},
 		global: {},
 	})
-	const [includeTaskHistoryInEnhance, setIncludeTaskHistoryInEnhance] = useState(false)
+	const [includeTaskHistoryInEnhance, setIncludeTaskHistoryInEnhance] = useState(true)
 
 	const setListApiConfigMeta = useCallback(
 		(value: ProviderSettingsEntry[]) => setState((prevState) => ({ ...prevState, listApiConfigMeta: value })),