fix: resolve merge conflict, use startBackgroundRetentionPurge() for cleaner code

- Resolved merge conflict in extension.ts, keeping extracted function approach
- startBackgroundRetentionPurge() encapsulates all purge logic in task-history-retention.ts
- Added getStorageBasePath mock to task-storage-size tests (addresses roomote review)

src/__tests__/extension.spec.ts

@@ -159,9 +159,9 @@ vi.mock("../utils/autoImportSettings", () => ({
 	autoImportSettings: vi.fn().mockResolvedValue(undefined),
 }))
 
-// Avoid filesystem access during activation by stubbing purge
+// Avoid filesystem access during activation by stubbing background purge
 vi.mock("../utils/task-history-retention", () => ({
-	purgeOldTasks: vi.fn().mockResolvedValue({ purgedCount: 0, cutoff: null }),
+	startBackgroundRetentionPurge: vi.fn(),
 }))
 
 // Ensure storage base path resolves to provided path to avoid touching VS Code config

src/extension.ts

@@ -44,7 +44,7 @@ import {
 } from "./activate"
 import { initializeI18n } from "./i18n"
 import { flushModels, initializeModelCacheRefresh, refreshModels } from "./api/providers/fetchers/modelCache"
-import { purgeOldTasks, RetentionSetting } from "./utils/task-history-retention"
+import { startBackgroundRetentionPurge } from "./utils/task-history-retention"
 
 /**
  * Built using https://github.com/microsoft/vscode-webview-ui-toolkit
@@ -389,42 +389,16 @@ export async function activate(context: vscode.ExtensionContext) {
 	vscode.commands.executeCommand(`${Package.name}.activationCompleted`)
 
 	// Task history retention purge (runs in background after activation)
-	// Fire-and-forget to avoid blocking extension startup
-	void (async () => {
-		try {
-			const config = vscode.workspace.getConfiguration(Package.name)
-			const retention = config.get<string>("taskHistoryRetention", "never") ?? "never"
-
-			// Skip if retention is disabled (default)
-			if (retention === "never") {
-				return
-			}
-
-			outputChannel.appendLine(`[Retention] Starting background purge: setting=${retention}`)
-
-			const result = await purgeOldTasks(
-				retention as RetentionSetting,
-				contextProxy.globalStorageUri.fsPath,
-				(m) => outputChannel.appendLine(m),
-				false,
-				async (taskId: string) => {
-					// Reuse the same internal deletion logic as the History view so that
-					// checkpoints, shadow repositories, and task state are cleaned up consistently.
-					await provider.deleteTaskWithId(taskId)
-				},
-			)
-
-			if (result.purgedCount > 0) {
-				outputChannel.appendLine(
-					`[Retention] Background purge complete: purged=${result.purgedCount}, cutoff=${result.cutoff ? new Date(result.cutoff).toISOString() : "none"}`,
-				)
-			}
-		} catch (error) {
-			outputChannel.appendLine(
-				`[Retention] Failed during background purge: ${error instanceof Error ? error.message : String(error)}`,
-			)
-		}
-	})()
+	// By this point, provider is fully initialized and ready to handle deletions
+	startBackgroundRetentionPurge({
+		globalStoragePath: contextProxy.globalStorageUri.fsPath,
+		log: (m) => outputChannel.appendLine(m),
+		deleteTaskById: async (taskId: string) => {
+			// Reuse the same internal deletion logic as the History view so that
+			// checkpoints, shadow repositories, and task state are cleaned up consistently.
+			await provider.deleteTaskWithId(taskId)
+		},
+	})
 
 	// Implements the `RooCodeAPI` interface.
 	const socketPath = process.env.ROO_CODE_IPC_SOCKET_PATH

src/utils/__tests__/task-storage-size.spec.ts

@@ -1,6 +1,11 @@
 import * as path from "path"
 import { calculateTaskStorageSize, formatBytes } from "../task-storage-size"
 
+// Mock storage to avoid VS Code config access during tests
+vi.mock("../storage", () => ({
+	getStorageBasePath: (p: string) => Promise.resolve(p),
+}))
+
 // Mock fs/promises
 const mockReaddir = vi.fn()
 const mockStat = vi.fn()

src/utils/task-history-retention.ts

@@ -1,9 +1,11 @@
+import * as vscode from "vscode"
 import * as path from "path"
 import * as fs from "fs/promises"
 import type { Dirent } from "fs"
 
 import { getStorageBasePath } from "./storage"
 import { GlobalFileNames } from "../shared/globalFileNames"
+import { Package } from "../shared/package"
 
 /**
  * Allowed retention day values (as numbers).
@@ -281,3 +283,72 @@ function normalizeDays(value: RetentionSetting): number {
 	const n = typeof value === "number" ? value : parseInt(String(value), 10)
 	return Number.isFinite(n) && n > 0 ? Math.trunc(n) : 0
 }
+
+/**
+ * Options for starting the background retention purge.
+ */
+export interface BackgroundPurgeOptions {
+	/** VS Code global storage fsPath */
+	globalStoragePath: string
+	/** Logger function */
+	log: (message: string) => void
+	/** Function to delete a task by ID (should use ClineProvider.deleteTaskWithId for full cleanup) */
+	deleteTaskById: (taskId: string, taskDirPath: string) => Promise<void>
+}
+
+/**
+ * Starts the task history retention purge in the background.
+ * This function is designed to be called after extension activation completes,
+ * using a fire-and-forget pattern (void) to avoid blocking activation.
+ *
+ * It reads the retention setting from VS Code configuration, executes the purge,
+ * and shows a notification if tasks were deleted.
+ *
+ * @param options Configuration options for the background purge
+ */
+export function startBackgroundRetentionPurge(options: BackgroundPurgeOptions): void {
+	const { globalStoragePath, log, deleteTaskById } = options
+
+	void (async () => {
+		try {
+			const config = vscode.workspace.getConfiguration(Package.name)
+			const retention = config.get<string>("taskHistoryRetention", "never") ?? "never"
+
+			// Skip if retention is disabled
+			if (retention === "never") {
+				log("[Retention] Background purge skipped: retention is set to 'never'")
+				return
+			}
+
+			log(`[Retention] Starting background purge: setting=${retention}`)
+
+			const result = await purgeOldTasks(
+				retention as RetentionSetting,
+				globalStoragePath,
+				log,
+				false,
+				deleteTaskById,
+			)
+
+			log(
+				`[Retention] Background purge complete: purged=${result.purgedCount}, cutoff=${result.cutoff ?? "none"}`,
+			)
+
+			// Show user notification if tasks were deleted
+			if (result.purgedCount > 0) {
+				const message = `Roo Code deleted ${result.purgedCount} task${result.purgedCount === 1 ? "" : "s"} older than ${retention} day${retention === "1" ? "" : "s"}`
+
+				vscode.window.showInformationMessage(message, "View Settings", "Dismiss").then((action) => {
+					if (action === "View Settings") {
+						vscode.commands.executeCommand(
+							"workbench.action.openSettings",
+							"roo-cline.taskHistoryRetention",
+						)
+					}
+				})
+			}
+		} catch (error) {
+			log(`[Retention] Failed during background purge: ${error instanceof Error ? error.message : String(error)}`)
+		}
+	})()
+}