diff --git a/src/extension.ts b/src/extension.ts
index 5db0996ad657..783e69b7e9b3 100644
--- a/src/extension.ts
+++ b/src/extension.ts
@@ -31,6 +31,7 @@ import { MdmService } from "./services/mdm/MdmService"
 import { migrateSettings } from "./utils/migrateSettings"
 import { autoImportSettings } from "./utils/autoImportSettings"
 import { API } from "./extension/api"
+import { notifyDevContainerStorageSetup } from "./utils/devContainer"
 
 import {
 	handleUri,
@@ -68,6 +69,22 @@ export async function activate(context: vscode.ExtensionContext) {
 	// Migrate old settings to new
 	await migrateSettings(context, outputChannel)
 
+	// Check for Dev Container and notify user about storage setup
+	const devContainerNotificationDismissed = context.globalState.get<boolean>(
+		"devContainerStorageNotificationDismissed",
+		false,
+	)
+	if (!devContainerNotificationDismissed) {
+		// Run this asynchronously so it doesn't block activation
+		setTimeout(() => {
+			notifyDevContainerStorageSetup(context).catch((error) => {
+				outputChannel.appendLine(
+					`[DevContainer] Failed to check Dev Container storage: ${error instanceof Error ? error.message : String(error)}`,
+				)
+			})
+		}, 3000) // Delay slightly to let the extension fully activate
+	}
+
 	// Initialize telemetry service.
 	const telemetryService = TelemetryService.createInstance()
 
diff --git a/src/utils/__tests__/devContainer.spec.ts b/src/utils/__tests__/devContainer.spec.ts
new file mode 100644
index 000000000000..cca30988987c
--- /dev/null
+++ b/src/utils/__tests__/devContainer.spec.ts
@@ -0,0 +1,393 @@
+import { describe, it, expect, vi, beforeEach, afterEach } from "vitest"
+import * as vscode from "vscode"
+import * as fs from "fs/promises"
+
+// Mock vscode module
+vi.mock("vscode", () => ({
+	env: {
+		remoteName: undefined,
+	},
+	workspace: {
+		workspaceFolders: undefined,
+		getConfiguration: vi.fn(),
+	},
+	window: {
+		showWarningMessage: vi.fn(),
+		showInformationMessage: vi.fn(),
+	},
+	ConfigurationTarget: {
+		Global: 1,
+	},
+}))
+
+// Mock fs/promises
+vi.mock("fs/promises", () => ({
+	default: {
+		mkdir: vi.fn(),
+		access: vi.fn(),
+		constants: {
+			R_OK: 4,
+			W_OK: 2,
+			X_OK: 1,
+		},
+	},
+	mkdir: vi.fn(),
+	access: vi.fn(),
+	constants: {
+		R_OK: 4,
+		W_OK: 2,
+		X_OK: 1,
+	},
+}))
+
+// Mock fs module
+vi.mock("fs", () => ({
+	accessSync: vi.fn(),
+	constants: {
+		F_OK: 0,
+	},
+}))
+
+// Import after mocks are set up
+import {
+	isRunningInDevContainer,
+	getDevContainerPersistentPath,
+	isEphemeralStoragePath,
+	notifyDevContainerStorageSetup,
+} from "../devContainer"
+
+describe("devContainer", () => {
+	beforeEach(() => {
+		// Reset all mocks
+		vi.clearAllMocks()
+		// Reset environment variables
+		delete process.env.REMOTE_CONTAINERS
+		delete process.env.CODESPACES
+		delete process.env.DEVCONTAINER
+		// Reset vscode.env.remoteName
+		;(vscode.env as any).remoteName = undefined
+	})
+
+	afterEach(() => {
+		vi.restoreAllMocks()
+	})
+
+	describe("isRunningInDevContainer", () => {
+		it("should return true when REMOTE_CONTAINERS env var is set", () => {
+			process.env.REMOTE_CONTAINERS = "true"
+			expect(isRunningInDevContainer()).toBe(true)
+		})
+
+		it("should return true when CODESPACES env var is set", () => {
+			process.env.CODESPACES = "true"
+			expect(isRunningInDevContainer()).toBe(true)
+		})
+
+		it("should return true when DEVCONTAINER env var is set", () => {
+			process.env.DEVCONTAINER = "true"
+			expect(isRunningInDevContainer()).toBe(true)
+		})
+
+		it("should return true when /.dockerenv file exists", async () => {
+			const fsModule = vi.mocked(await import("fs"))
+			fsModule.accessSync.mockImplementation(() => {
+				// Success - file exists
+				return undefined
+			})
+			expect(isRunningInDevContainer()).toBe(true)
+		})
+
+		it("should return false when /.dockerenv file does not exist", async () => {
+			const fsModule = vi.mocked(await import("fs"))
+			fsModule.accessSync.mockImplementation(() => {
+				throw new Error("File not found")
+			})
+			;(vscode.env as any).remoteName = undefined
+			expect(isRunningInDevContainer()).toBe(false)
+		})
+
+		it("should return true when VSCode remoteName contains 'container'", async () => {
+			const fsModule = vi.mocked(await import("fs"))
+			;(vscode.env as any).remoteName = "dev-container"
+			fsModule.accessSync.mockImplementation(() => {
+				throw new Error("File not found")
+			})
+			expect(isRunningInDevContainer()).toBe(true)
+		})
+
+		it("should return false when not in a container", async () => {
+			const fsModule = vi.mocked(await import("fs"))
+			fsModule.accessSync.mockImplementation(() => {
+				throw new Error("File not found")
+			})
+			;(vscode.env as any).remoteName = "ssh-remote"
+			expect(isRunningInDevContainer()).toBe(false)
+		})
+	})
+
+	describe("getDevContainerPersistentPath", () => {
+		it("should return null when not in a Dev Container", async () => {
+			// Ensure we're not in a Dev Container
+			const fsModule = vi.mocked(await import("fs"))
+			fsModule.accessSync.mockImplementation(() => {
+				throw new Error("File not found")
+			})
+			const result = await getDevContainerPersistentPath()
+			expect(result).toBe(null)
+		})
+
+		it("should return workspace-relative path when available and writable", async () => {
+			process.env.DEVCONTAINER = "true"
+			;(vscode.workspace as any).workspaceFolders = [
+				{
+					uri: {
+						fsPath: "/workspace/myproject",
+					},
+				},
+			]
+
+			const mockMkdir = vi.mocked(fs.mkdir)
+			const mockAccess = vi.mocked(fs.access)
+
+			mockMkdir.mockResolvedValue(undefined)
+			mockAccess.mockResolvedValue(undefined)
+
+			const result = await getDevContainerPersistentPath()
+			expect(result).toBe("/workspace/myproject/.roo-data")
+			expect(mockMkdir).toHaveBeenCalledWith("/workspace/myproject/.roo-data", { recursive: true })
+		})
+
+		it("should try alternative paths when primary path fails", async () => {
+			process.env.DEVCONTAINER = "true"
+			;(vscode.workspace as any).workspaceFolders = [
+				{
+					uri: {
+						fsPath: "/workspace/myproject",
+					},
+				},
+			]
+
+			const mockMkdir = vi.mocked(fs.mkdir)
+			const mockAccess = vi.mocked(fs.access)
+
+			// First path fails
+			mockMkdir.mockRejectedValueOnce(new Error("Permission denied"))
+			// Second path succeeds
+			mockMkdir.mockResolvedValueOnce(undefined)
+			mockAccess.mockResolvedValueOnce(undefined)
+
+			const result = await getDevContainerPersistentPath()
+			expect(result).toBe("/workspaces/.roo-data")
+		})
+
+		it("should return null when all paths fail", async () => {
+			process.env.DEVCONTAINER = "true"
+			;(vscode.workspace as any).workspaceFolders = [
+				{
+					uri: {
+						fsPath: "/workspace/myproject",
+					},
+				},
+			]
+
+			const mockMkdir = vi.mocked(fs.mkdir)
+			mockMkdir.mockRejectedValue(new Error("Permission denied"))
+
+			const result = await getDevContainerPersistentPath()
+			expect(result).toBe(null)
+		})
+	})
+
+	describe("isEphemeralStoragePath", () => {
+		it("should return false when not in a Dev Container", async () => {
+			const fsModule = vi.mocked(await import("fs"))
+			fsModule.accessSync.mockImplementation(() => {
+				throw new Error("File not found")
+			})
+			expect(isEphemeralStoragePath("/some/path")).toBe(false)
+		})
+
+		it("should return true for /tmp paths in Dev Container", () => {
+			process.env.DEVCONTAINER = "true"
+			expect(isEphemeralStoragePath("/tmp/storage")).toBe(true)
+		})
+
+		it("should return true for VSCode server paths in Dev Container", () => {
+			process.env.DEVCONTAINER = "true"
+			expect(isEphemeralStoragePath("/.vscode-server/data")).toBe(true)
+			expect(isEphemeralStoragePath("/.vscode-remote/extensions")).toBe(true)
+			expect(isEphemeralStoragePath("/home/user/.vscode/storage")).toBe(true)
+		})
+
+		it("should return true for paths containing temp directories", () => {
+			process.env.DEVCONTAINER = "true"
+			expect(isEphemeralStoragePath("/var/tmp/storage")).toBe(true)
+			expect(isEphemeralStoragePath("/home/user/tmp/data")).toBe(true)
+			expect(isEphemeralStoragePath("/dev/shm/cache")).toBe(true)
+		})
+
+		it("should return false for persistent paths in Dev Container", () => {
+			process.env.DEVCONTAINER = "true"
+			expect(isEphemeralStoragePath("/workspace/.roo-data")).toBe(false)
+			expect(isEphemeralStoragePath("/home/user/.roo-data")).toBe(false)
+			expect(isEphemeralStoragePath("/data/storage")).toBe(false)
+		})
+	})
+
+	describe("notifyDevContainerStorageSetup", () => {
+		it("should not show notification when not in Dev Container", async () => {
+			const fsModule = vi.mocked(await import("fs"))
+			fsModule.accessSync.mockImplementation(() => {
+				throw new Error("File not found")
+			})
+
+			const mockContext = {
+				globalStorageUri: { fsPath: "/normal/storage" },
+				globalState: {
+					update: vi.fn(),
+					get: vi.fn(),
+				},
+			}
+
+			await notifyDevContainerStorageSetup(mockContext as any)
+			expect(vscode.window.showWarningMessage).not.toHaveBeenCalled()
+		})
+
+		it("should not show notification when storage path is not ephemeral", async () => {
+			process.env.DEVCONTAINER = "true"
+
+			const mockContext = {
+				globalStorageUri: { fsPath: "/workspace/.roo-data" },
+				globalState: {
+					update: vi.fn(),
+					get: vi.fn(),
+				},
+			}
+
+			await notifyDevContainerStorageSetup(mockContext as any)
+			expect(vscode.window.showWarningMessage).not.toHaveBeenCalled()
+		})
+
+		it("should show notification when in Dev Container with ephemeral storage", async () => {
+			process.env.DEVCONTAINER = "true"
+			;(vscode.workspace as any).workspaceFolders = [
+				{
+					uri: {
+						fsPath: "/workspace/myproject",
+					},
+				},
+			]
+
+			const mockMkdir = vi.mocked(fs.mkdir)
+			const mockAccess = vi.mocked(fs.access)
+			mockMkdir.mockResolvedValue(undefined)
+			mockAccess.mockResolvedValue(undefined)
+
+			const mockShowWarningMessage = vi.mocked(vscode.window.showWarningMessage)
+			mockShowWarningMessage.mockResolvedValue("Configure Now" as any)
+
+			const mockConfig = {
+				update: vi.fn().mockResolvedValue(undefined),
+			}
+			vi.mocked(vscode.workspace.getConfiguration).mockReturnValue(mockConfig as any)
+
+			const mockContext = {
+				globalStorageUri: { fsPath: "/.vscode-server/data/storage" },
+				globalState: {
+					update: vi.fn(),
+					get: vi.fn().mockReturnValue(false),
+				},
+			}
+
+			await notifyDevContainerStorageSetup(mockContext as any)
+
+			expect(mockShowWarningMessage).toHaveBeenCalledWith(
+				expect.stringContaining("Dev Container"),
+				"Configure Now",
+				"Remind Me Later",
+				"Don't Show Again",
+			)
+
+			expect(mockConfig.update).toHaveBeenCalledWith(
+				"customStoragePath",
+				"/workspace/myproject/.roo-data",
+				vscode.ConfigurationTarget.Global,
+			)
+
+			expect(vscode.window.showInformationMessage).toHaveBeenCalledWith(
+				expect.stringContaining("Storage path set to"),
+			)
+		})
+
+		it("should update global state when user chooses 'Don't Show Again'", async () => {
+			process.env.DEVCONTAINER = "true"
+			;(vscode.workspace as any).workspaceFolders = [
+				{
+					uri: {
+						fsPath: "/workspace/myproject",
+					},
+				},
+			]
+
+			const mockMkdir = vi.mocked(fs.mkdir)
+			const mockAccess = vi.mocked(fs.access)
+			mockMkdir.mockResolvedValue(undefined)
+			mockAccess.mockResolvedValue(undefined)
+
+			const mockShowWarningMessage = vi.mocked(vscode.window.showWarningMessage)
+			mockShowWarningMessage.mockResolvedValue("Don't Show Again" as any)
+
+			const mockContext = {
+				globalStorageUri: { fsPath: "/.vscode-server/data/storage" },
+				globalState: {
+					update: vi.fn(),
+					get: vi.fn().mockReturnValue(false),
+				},
+			}
+
+			await notifyDevContainerStorageSetup(mockContext as any)
+
+			expect(mockContext.globalState.update).toHaveBeenCalledWith(
+				"devContainerStorageNotificationDismissed",
+				true,
+			)
+		})
+
+		it("should not configure when user chooses 'Remind Me Later'", async () => {
+			process.env.DEVCONTAINER = "true"
+			;(vscode.workspace as any).workspaceFolders = [
+				{
+					uri: {
+						fsPath: "/workspace/myproject",
+					},
+				},
+			]
+
+			const mockMkdir = vi.mocked(fs.mkdir)
+			const mockAccess = vi.mocked(fs.access)
+			mockMkdir.mockResolvedValue(undefined)
+			mockAccess.mockResolvedValue(undefined)
+
+			const mockShowWarningMessage = vi.mocked(vscode.window.showWarningMessage)
+			mockShowWarningMessage.mockResolvedValue("Remind Me Later" as any)
+
+			const mockConfig = {
+				update: vi.fn(),
+			}
+			vi.mocked(vscode.workspace.getConfiguration).mockReturnValue(mockConfig as any)
+
+			const mockContext = {
+				globalStorageUri: { fsPath: "/.vscode-server/data/storage" },
+				globalState: {
+					update: vi.fn(),
+					get: vi.fn().mockReturnValue(false),
+				},
+			}
+
+			await notifyDevContainerStorageSetup(mockContext as any)
+
+			expect(mockConfig.update).not.toHaveBeenCalled()
+			expect(mockContext.globalState.update).not.toHaveBeenCalled()
+		})
+	})
+})
diff --git a/src/utils/devContainer.ts b/src/utils/devContainer.ts
new file mode 100644
index 000000000000..90b5a2edf8a2
--- /dev/null
+++ b/src/utils/devContainer.ts
@@ -0,0 +1,143 @@
+import * as vscode from "vscode"
+import * as fs from "fs/promises"
+import * as fsSync from "fs"
+import * as path from "path"
+
+/**
+ * Checks if the current environment is running inside a Dev Container
+ * @returns true if running in a Dev Container, false otherwise
+ */
+export function isRunningInDevContainer(): boolean {
+	// Check for common Dev Container environment variables
+	if (process.env.REMOTE_CONTAINERS || process.env.CODESPACES || process.env.DEVCONTAINER) {
+		return true
+	}
+
+	// Check if running in a container by looking for .dockerenv file
+	try {
+		const dockerEnvPath = "/.dockerenv"
+		fsSync.accessSync(dockerEnvPath, fsSync.constants.F_OK)
+		return true
+	} catch {
+		// File doesn't exist, not in Docker container
+	}
+
+	// Check VSCode's remote name for devcontainer
+	const remoteName = vscode.env.remoteName
+	if (remoteName && remoteName.toLowerCase().includes("container")) {
+		return true
+	}
+
+	return false
+}
+
+/**
+ * Gets the recommended persistent storage path for Dev Containers
+ * This should be a path that persists across container rebuilds
+ * @returns Recommended storage path or null if not applicable
+ */
+export async function getDevContainerPersistentPath(): Promise<string | null> {
+	if (!isRunningInDevContainer()) {
+		return null
+	}
+
+	// Check for workspace folder that might be mounted from host
+	const workspaceFolders = vscode.workspace.workspaceFolders
+	if (workspaceFolders && workspaceFolders.length > 0) {
+		const workspaceRoot = workspaceFolders[0].uri.fsPath
+
+		// Try common persistent mount points in Dev Containers
+		const possiblePaths = [
+			path.join(workspaceRoot, ".roo-data"), // Within workspace (persists if workspace is mounted)
+			"/workspaces/.roo-data", // Common devcontainer workspace mount
+			"/home/vscode/.roo-data", // User home in standard devcontainer
+			"/root/.roo-data", // Root user home
+		]
+
+		for (const testPath of possiblePaths) {
+			try {
+				// Test if we can create and access this directory
+				await fs.mkdir(testPath, { recursive: true })
+				await fs.access(testPath, fs.constants.R_OK | fs.constants.W_OK)
+				return testPath
+			} catch {
+				// This path is not suitable, try next
+				continue
+			}
+		}
+	}
+
+	return null
+}
+
+/**
+ * Checks if the storage path will be lost on container rebuild
+ * @param storagePath The current storage path
+ * @returns true if the path is ephemeral (will be lost on rebuild)
+ */
+export function isEphemeralStoragePath(storagePath: string): boolean {
+	if (!isRunningInDevContainer()) {
+		return false
+	}
+
+	// Common ephemeral paths in containers
+	const ephemeralPaths = [
+		"/tmp",
+		"/var/tmp",
+		"/dev/shm",
+		"/.vscode-server",
+		"/.vscode-remote",
+		"/.vscode-server-insiders",
+	]
+
+	const normalizedPath = path.normalize(storagePath).toLowerCase()
+
+	return ephemeralPaths.some(
+		(ephemeral) =>
+			normalizedPath.startsWith(ephemeral.toLowerCase()) ||
+			normalizedPath.includes("/.vscode") ||
+			normalizedPath.includes("/vscode-") ||
+			normalizedPath.includes("/tmp/") ||
+			normalizedPath.includes("/temp/"),
+	)
+}
+
+/**
+ * Shows a notification to the user about Dev Container storage configuration
+ * @param context The extension context
+ */
+export async function notifyDevContainerStorageSetup(context: vscode.ExtensionContext): Promise<void> {
+	const currentStoragePath = context.globalStorageUri.fsPath
+
+	if (!isRunningInDevContainer() || !isEphemeralStoragePath(currentStoragePath)) {
+		return
+	}
+
+	const recommendedPath = await getDevContainerPersistentPath()
+	if (!recommendedPath) {
+		return
+	}
+
+	const message =
+		"You're using Roo Code in a Dev Container. Your task history may be lost when the container is rebuilt. Would you like to configure a persistent storage path?"
+
+	const choice = await vscode.window.showWarningMessage(
+		message,
+		"Configure Now",
+		"Remind Me Later",
+		"Don't Show Again",
+	)
+
+	if (choice === "Configure Now") {
+		// Set the recommended path
+		const config = vscode.workspace.getConfiguration("roo-code")
+		await config.update("customStoragePath", recommendedPath, vscode.ConfigurationTarget.Global)
+
+		vscode.window.showInformationMessage(
+			`Storage path set to: ${recommendedPath}. Your task history will now persist across container rebuilds.`,
+		)
+	} else if (choice === "Don't Show Again") {
+		// Store a flag to not show this again
+		await context.globalState.update("devContainerStorageNotificationDismissed", true)
+	}
+}
diff --git a/src/utils/storage.ts b/src/utils/storage.ts
index 5125d6cf4497..e7cbe9418d0f 100644
--- a/src/utils/storage.ts
+++ b/src/utils/storage.ts
@@ -5,10 +5,12 @@ import { constants as fsConstants } from "fs"
 
 import { Package } from "../shared/package"
 import { t } from "../i18n"
+import { isRunningInDevContainer, getDevContainerPersistentPath, isEphemeralStoragePath } from "./devContainer"
 
 /**
  * Gets the base storage path for conversations
  * If a custom path is configured, uses that path
+ * For Dev Containers with ephemeral storage, suggests a persistent path
  * Otherwise uses the default VSCode extension global storage path
  */
 export async function getStorageBasePath(defaultPath: string): Promise<string> {
@@ -24,8 +26,17 @@ export async function getStorageBasePath(defaultPath: string): Promise<string> {
 		return defaultPath
 	}
 
-	// If no custom path is set, use default path
+	// If no custom path is set, check for Dev Container
 	if (!customStoragePath) {
+		// Check if we're in a Dev Container with ephemeral storage
+		if (isRunningInDevContainer() && isEphemeralStoragePath(defaultPath)) {
+			// Try to get a persistent path for Dev Container
+			const persistentPath = await getDevContainerPersistentPath()
+			if (persistentPath) {
+				console.info(`Dev Container detected: Using persistent storage path ${persistentPath}`)
+				return persistentPath
+			}
+		}
 		return defaultPath
 	}