diff --git a/src/utils/__tests__/migrateSettings.spec.ts b/src/utils/__tests__/migrateSettings.spec.ts
index 924d249986..215b7b4593 100644
--- a/src/utils/__tests__/migrateSettings.spec.ts
+++ b/src/utils/__tests__/migrateSettings.spec.ts
@@ -4,6 +4,7 @@ import type { ContextProxy } from "../../core/config/ContextProxy"
 import type { HistoryItem } from "@roo-code/types"
 
 describe("migrateTaskHistoryWithContextProxy", () => {
+	let mockContext: any
 	let mockContextProxy: any
 	let mockWorkspaceFolder: any
 
@@ -19,7 +20,7 @@ describe("migrateTaskHistoryWithContextProxy", () => {
 		}
 
 		// Mock VSCode context
-		const mockContext = {
+		mockContext = {
 			globalState: {
 				get: vi.fn(),
 				update: vi.fn(),
@@ -37,7 +38,6 @@ describe("migrateTaskHistoryWithContextProxy", () => {
 			updateWorkspaceState: vi.fn(),
 			getWorkspaceState: vi.fn(),
 			getWorkspaceSettings: vi.fn(),
-			context: mockContext,
 		} as any
 	})
 
@@ -83,16 +83,19 @@ describe("migrateTaskHistoryWithContextProxy", () => {
 		]
 
 		// Mock context.globalState.get to return the raw state with taskHistory
-		vi.mocked(mockContextProxy.context.globalState.get).mockImplementation((key: string, defaultValue?: any) => {
+		vi.mocked(mockContext.globalState.get).mockImplementation((key: string, defaultValue?: any) => {
 			if (key === "globalSettings") {
 				return { taskHistory: mockTaskHistory }
 			}
+			if (key === "taskHistoryMigratedToWorkspace") {
+				return false
+			}
 			return defaultValue
 		})
 		vi.mocked(mockContextProxy.getWorkspaceSettings).mockReturnValue({})
 
 		// Act
-		await migrateTaskHistoryWithContextProxy(mockContextProxy, mockWorkspaceFolder)
+		await migrateTaskHistoryWithContextProxy(mockContext, mockContextProxy, mockWorkspaceFolder)
 
 		// Assert
 		// Should update workspace state with only tasks from current workspace
@@ -102,45 +105,51 @@ describe("migrateTaskHistoryWithContextProxy", () => {
 		])
 
 		// Should update global state to keep only tasks from other workspaces
-		expect(mockContextProxy.context.globalState.update).toHaveBeenCalledWith("globalSettings", {
+		expect(mockContext.globalState.update).toHaveBeenCalledWith("globalSettings", {
 			taskHistory: [mockTaskHistory[2]],
 		})
 	})
 
 	it("should handle empty task history in global state", async () => {
 		// Arrange
-		vi.mocked(mockContextProxy.context.globalState.get).mockImplementation((key: string) => {
+		vi.mocked(mockContext.globalState.get).mockImplementation((key: string) => {
 			if (key === "globalSettings") {
 				return { taskHistory: [] }
 			}
+			if (key === "taskHistoryMigratedToWorkspace") {
+				return false
+			}
 			return undefined
 		})
 		vi.mocked(mockContextProxy.getWorkspaceSettings).mockReturnValue({})
 
 		// Act
-		await migrateTaskHistoryWithContextProxy(mockContextProxy, mockWorkspaceFolder)
+		await migrateTaskHistoryWithContextProxy(mockContext, mockContextProxy, mockWorkspaceFolder)
 
 		// Assert
 		expect(mockContextProxy.updateWorkspaceState).not.toHaveBeenCalled()
-		expect(mockContextProxy.context.globalState.update).not.toHaveBeenCalled()
+		expect(mockContext.globalState.update).not.toHaveBeenCalled()
 	})
 
 	it("should handle undefined task history in global state", async () => {
 		// Arrange
-		vi.mocked(mockContextProxy.context.globalState.get).mockImplementation((key: string) => {
+		vi.mocked(mockContext.globalState.get).mockImplementation((key: string) => {
 			if (key === "globalSettings") {
 				return {}
 			}
+			if (key === "taskHistoryMigratedToWorkspace") {
+				return false
+			}
 			return undefined
 		})
 		vi.mocked(mockContextProxy.getWorkspaceSettings).mockReturnValue({})
 
 		// Act
-		await migrateTaskHistoryWithContextProxy(mockContextProxy, mockWorkspaceFolder)
+		await migrateTaskHistoryWithContextProxy(mockContext, mockContextProxy, mockWorkspaceFolder)
 
 		// Assert
 		expect(mockContextProxy.updateWorkspaceState).not.toHaveBeenCalled()
-		expect(mockContextProxy.context.globalState.update).not.toHaveBeenCalled()
+		expect(mockContext.globalState.update).not.toHaveBeenCalled()
 	})
 
 	it("should merge with existing workspace task history", async () => {
@@ -171,16 +180,19 @@ describe("migrateTaskHistoryWithContextProxy", () => {
 			workspace: "/test/workspace",
 		}
 
-		vi.mocked(mockContextProxy.context.globalState.get).mockImplementation((key: string) => {
+		vi.mocked(mockContext.globalState.get).mockImplementation((key: string) => {
 			if (key === "globalSettings") {
 				return { taskHistory: [globalTask] }
 			}
+			if (key === "taskHistoryMigratedToWorkspace") {
+				return false
+			}
 			return undefined
 		})
 		vi.mocked(mockContextProxy.getWorkspaceSettings).mockReturnValue({ taskHistory: [existingWorkspaceTask] })
 
 		// Act
-		await migrateTaskHistoryWithContextProxy(mockContextProxy, mockWorkspaceFolder)
+		await migrateTaskHistoryWithContextProxy(mockContext, mockContextProxy, mockWorkspaceFolder)
 
 		// Assert
 		// Should merge tasks, keeping both existing and migrated
@@ -190,7 +202,7 @@ describe("migrateTaskHistoryWithContextProxy", () => {
 		])
 
 		// Should clear the migrated task from global state
-		expect(mockContextProxy.context.globalState.update).toHaveBeenCalledWith("globalSettings", {})
+		expect(mockContext.globalState.update).toHaveBeenCalledWith("globalSettings", {})
 	})
 
 	it("should handle tasks without workspacePath", async () => {
@@ -208,29 +220,89 @@ describe("migrateTaskHistoryWithContextProxy", () => {
 			// No workspace property
 		} as HistoryItem
 
-		vi.mocked(mockContextProxy.context.globalState.get).mockImplementation((key: string) => {
+		vi.mocked(mockContext.globalState.get).mockImplementation((key: string) => {
 			if (key === "globalSettings") {
 				return { taskHistory: [taskWithoutPath] }
 			}
+			if (key === "taskHistoryMigratedToWorkspace") {
+				return false
+			}
 			return undefined
 		})
 		vi.mocked(mockContextProxy.getWorkspaceSettings).mockReturnValue({})
 
 		// Act
-		await migrateTaskHistoryWithContextProxy(mockContextProxy, mockWorkspaceFolder)
+		await migrateTaskHistoryWithContextProxy(mockContext, mockContextProxy, mockWorkspaceFolder)
 
 		// Assert
 		// Should not migrate tasks without workspace path
 		expect(mockContextProxy.updateWorkspaceState).not.toHaveBeenCalled()
 		// Should keep the task in global state
-		expect(mockContextProxy.context.globalState.update).toHaveBeenCalledWith("globalSettings", {
+		expect(mockContext.globalState.update).toHaveBeenCalledWith("globalSettings", {
 			taskHistory: [taskWithoutPath],
 		})
 	})
 
 	it("should handle no workspace folder", async () => {
 		// Arrange
-		vi.mocked(mockContextProxy.context.globalState.get).mockImplementation((key: string) => {
+		vi.mocked(mockContext.globalState.get).mockImplementation((key: string) => {
+			if (key === "globalSettings") {
+				return {
+					taskHistory: [
+						{
+							id: "task1",
+							number: 1,
+							ts: Date.now(),
+							task: "Test task",
+							tokensIn: 100,
+							tokensOut: 50,
+							cacheWrites: 0,
+							cacheReads: 0,
+							totalCost: 0.01,
+							workspace: "/test/workspace",
+						},
+					],
+				}
+			}
+			if (key === "taskHistoryMigratedToWorkspace") {
+				return false
+			}
+			return undefined
+		})
+
+		// Act
+		await migrateTaskHistoryWithContextProxy(mockContext, mockContextProxy, undefined)
+
+		// Assert
+		// Should not perform any migration without a workspace
+		expect(mockContextProxy.updateWorkspaceState).not.toHaveBeenCalled()
+		expect(mockContext.globalState.update).not.toHaveBeenCalled()
+	})
+
+	it("should handle errors gracefully", async () => {
+		// Arrange
+		const consoleSpy = vi.spyOn(console, "error").mockImplementation(() => {})
+		vi.mocked(mockContext.globalState.get).mockImplementation(() => {
+			throw new Error("Failed to get global state")
+		})
+
+		// Act
+		await migrateTaskHistoryWithContextProxy(mockContext, mockContextProxy, mockWorkspaceFolder)
+
+		// Assert
+		expect(consoleSpy).toHaveBeenCalledWith("Failed to migrate task history to workspace:", expect.any(Error))
+		expect(mockContextProxy.updateWorkspaceState).not.toHaveBeenCalled()
+		expect(mockContext.globalState.update).not.toHaveBeenCalled()
+
+		consoleSpy.mockRestore()
+	})
+
+	it("should skip migration if already migrated", async () => {
+		// Arrange
+		vi.mocked(mockContext.globalState.get).mockImplementation((key: string) => {
+			if (key === "taskHistoryMigratedToWorkspace") {
+				return true // Already migrated
+			}
 			if (key === "globalSettings") {
 				return {
 					taskHistory: [
@@ -253,29 +325,47 @@ describe("migrateTaskHistoryWithContextProxy", () => {
 		})
 
 		// Act
-		await migrateTaskHistoryWithContextProxy(mockContextProxy, undefined)
+		await migrateTaskHistoryWithContextProxy(mockContext, mockContextProxy, mockWorkspaceFolder)
 
 		// Assert
-		// Should not perform any migration without a workspace
+		// Should not perform any migration operations
 		expect(mockContextProxy.updateWorkspaceState).not.toHaveBeenCalled()
-		expect(mockContextProxy.context.globalState.update).not.toHaveBeenCalled()
+		expect(mockContext.globalState.update).not.toHaveBeenCalled()
 	})
 
-	it("should handle errors gracefully", async () => {
+	it("should set migration flag after successful migration", async () => {
 		// Arrange
-		const consoleSpy = vi.spyOn(console, "error").mockImplementation(() => {})
-		vi.mocked(mockContextProxy.context.globalState.get).mockImplementation(() => {
-			throw new Error("Failed to get global state")
+		const mockTaskHistory: HistoryItem[] = [
+			{
+				id: "task1",
+				number: 1,
+				ts: Date.now(),
+				task: "Test task",
+				tokensIn: 100,
+				tokensOut: 50,
+				cacheWrites: 0,
+				cacheReads: 0,
+				totalCost: 0.01,
+				workspace: "/test/workspace",
+			},
+		]
+
+		vi.mocked(mockContext.globalState.get).mockImplementation((key: string) => {
+			if (key === "globalSettings") {
+				return { taskHistory: mockTaskHistory }
+			}
+			if (key === "taskHistoryMigratedToWorkspace") {
+				return false
+			}
+			return undefined
 		})
+		vi.mocked(mockContextProxy.getWorkspaceSettings).mockReturnValue({})
 
 		// Act
-		await migrateTaskHistoryWithContextProxy(mockContextProxy, mockWorkspaceFolder)
+		await migrateTaskHistoryWithContextProxy(mockContext, mockContextProxy, mockWorkspaceFolder)
 
 		// Assert
-		expect(consoleSpy).toHaveBeenCalledWith("Failed to migrate task history to workspace:", expect.any(Error))
-		expect(mockContextProxy.updateWorkspaceState).not.toHaveBeenCalled()
-		expect(mockContextProxy.context.globalState.update).not.toHaveBeenCalled()
-
-		consoleSpy.mockRestore()
+		// Should set the migration flag
+		expect(mockContext.globalState.update).toHaveBeenCalledWith("taskHistoryMigratedToWorkspace", true)
 	})
 })
diff --git a/src/utils/migrateSettings.ts b/src/utils/migrateSettings.ts
index 7f0cab8dfd..389fdbc986 100644
--- a/src/utils/migrateSettings.ts
+++ b/src/utils/migrateSettings.ts
@@ -134,16 +134,15 @@ export async function migrateTaskHistoryWithContextProxy(
 	contextProxy: ContextProxy,
 	workspaceFolder: vscode.WorkspaceFolder | undefined,
 ): Promise<void> {
-	const alreadyMigrated = context.globalState.get<boolean>(TASK_HISTORY_MIGRATION_KEY)
-	if (alreadyMigrated) {
-		return
-	}
-
-	if (!workspaceFolder) {
-		return
-	}
-
 	try {
+		const alreadyMigrated = context.globalState.get<boolean>(TASK_HISTORY_MIGRATION_KEY)
+		if (alreadyMigrated) {
+			return
+		}
+
+		if (!workspaceFolder) {
+			return
+		}
 		// Get the raw global state directly from context
 		const rawGlobalState = context.globalState.get<any>("globalSettings", {})
 		const taskHistory = rawGlobalState.taskHistory as HistoryItem[] | undefined