diff --git a/src/core/Cline.ts b/src/core/Cline.ts
index c66dec2c86..b9b243dbc1 100644
--- a/src/core/Cline.ts
+++ b/src/core/Cline.ts
@@ -10,10 +10,10 @@ import getFolderSize from "get-folder-size"
 import * as path from "path"
 import { serializeError } from "serialize-error"
 import * as vscode from "vscode"
-import { ApiHandler, SingleCompletionHandler, buildApiHandler } from "../api"
+import { ApiHandler, buildApiHandler } from "../api"
 import { ApiStream } from "../api/transform/stream"
 import { DIFF_VIEW_URI_SCHEME, DiffViewProvider } from "../integrations/editor/DiffViewProvider"
-import { CheckpointService, CheckpointServiceFactory } from "../services/checkpoints"
+import { ShadowCheckpointService } from "../services/checkpoints/ShadowCheckpointService"
 import { findToolName, formatContentBlockToMarkdown } from "../integrations/misc/export-markdown"
 import {
 	extractTextFromFile,
@@ -116,7 +116,7 @@ export class Cline {
 
 	// checkpoints
 	enableCheckpoints: boolean = false
-	private checkpointService?: CheckpointService
+	private checkpointService?: ShadowCheckpointService
 
 	// streaming
 	isWaitingForFirstChunk = false
@@ -747,8 +747,11 @@ export class Cline {
 	}
 
 	private async initiateTaskLoop(userContent: UserContent): Promise<void> {
+		this.initializeCheckpoints()
+
 		let nextUserContent = userContent
 		let includeFileDetails = true
+
 		while (!this.abort) {
 			const didEndLoop = await this.recursivelyMakeClineRequests(nextUserContent, includeFileDetails)
 			includeFileDetails = false // we only need file details the first time
@@ -2773,7 +2776,7 @@ export class Cline {
 		}
 
 		if (isCheckpointPossible) {
-			await this.checkpointSave({ isFirst: false })
+			this.checkpointSave()
 		}
 
 		/*
@@ -2839,13 +2842,6 @@ export class Cline {
 		// get previous api req's index to check token usage and determine if we need to truncate conversation history
 		const previousApiReqIndex = findLastIndex(this.clineMessages, (m) => m.say === "api_req_started")
 
-		// Save checkpoint if this is the first API request.
-		const isFirstRequest = this.clineMessages.filter((m) => m.say === "api_req_started").length === 0
-
-		if (isFirstRequest) {
-			await this.checkpointSave({ isFirst: true })
-		}
-
 		// getting verbose details is an expensive operation, it uses globby to top-down build file structure of project which for large projects can take a few seconds
 		// for the best UX we show a placeholder api_req_started message with a loading spinner as this happens
 		await this.say(
@@ -3356,37 +3352,88 @@ export class Cline {
 
 	// Checkpoints
 
-	private async getCheckpointService() {
+	private async initializeCheckpoints() {
 		if (!this.enableCheckpoints) {
-			throw new Error("Checkpoints are disabled")
+			return
 		}
 
-		if (!this.checkpointService) {
+		const log = (message: string) => {
+			console.log(message)
+
+			try {
+				this.providerRef.deref()?.log(message)
+			} catch (err) {
+				// NO-OP
+			}
+		}
+
+		try {
+			if (this.checkpointService) {
+				log("[Cline#initializeCheckpoints] checkpointService already initialized")
+				return
+			}
+
 			const workspaceDir = vscode.workspace.workspaceFolders?.map((folder) => folder.uri.fsPath).at(0)
-			const shadowDir = this.providerRef.deref()?.context.globalStorageUri.fsPath
 
 			if (!workspaceDir) {
-				this.providerRef.deref()?.log("[getCheckpointService] workspace folder not found")
-				throw new Error("Workspace directory not found")
+				log("[Cline#initializeCheckpoints] workspace folder not found, disabling checkpoints")
+				this.enableCheckpoints = false
+				return
 			}
 
+			const shadowDir = this.providerRef.deref()?.context.globalStorageUri.fsPath
+
 			if (!shadowDir) {
-				this.providerRef.deref()?.log("[getCheckpointService] shadowDir not found")
-				throw new Error("Global storage directory not found")
+				log("[Cline#initializeCheckpoints] shadowDir not found, disabling checkpoints")
+				this.enableCheckpoints = false
+				return
 			}
 
-			this.checkpointService = await CheckpointServiceFactory.create({
-				strategy: "shadow",
-				options: {
-					taskId: this.taskId,
-					workspaceDir,
-					shadowDir,
-					log: (message) => this.providerRef.deref()?.log(message),
-				},
-			})
-		}
+			const service = await ShadowCheckpointService.create({ taskId: this.taskId, workspaceDir, shadowDir, log })
 
-		return this.checkpointService
+			if (!service) {
+				log("[Cline#initializeCheckpoints] failed to create checkpoint service, disabling checkpoints")
+				this.enableCheckpoints = false
+				return
+			}
+
+			service.on("initialize", ({ workspaceDir, created, duration }) => {
+				try {
+					if (created) {
+						log(`[Cline#initializeCheckpoints] created new shadow repo (${workspaceDir}) in ${duration}ms`)
+					} else {
+						log(
+							`[Cline#initializeCheckpoints] found existing shadow repo (${workspaceDir}) in ${duration}ms`,
+						)
+					}
+
+					this.checkpointService = service
+					this.checkpointSave()
+				} catch (err) {
+					log("[Cline#initializeCheckpoints] caught error in on('initialize'), disabling checkpoints")
+					this.enableCheckpoints = false
+				}
+			})
+
+			service.on("checkpoint", ({ isFirst, fromHash: from, toHash: to }) => {
+				try {
+					log(`[Cline#initializeCheckpoints] ${isFirst ? "initial" : "incremental"} checkpoint saved: ${to}`)
+					this.providerRef.deref()?.postMessageToWebview({ type: "currentCheckpointUpdated", text: to })
+
+					this.say("checkpoint_saved", to, undefined, undefined, { isFirst, from, to }).catch((e) =>
+						console.error("Error saving checkpoint message:", e),
+					)
+				} catch (err) {
+					log("[Cline#initializeCheckpoints] caught error in on('checkpoint'), disabling checkpoints")
+					this.enableCheckpoints = false
+				}
+			})
+
+			service.initShadowGit()
+		} catch (err) {
+			log("[Cline#initializeCheckpoints] caught error in initializeCheckpoints(), disabling checkpoints")
+			this.enableCheckpoints = false
+		}
 	}
 
 	public async checkpointDiff({
@@ -3398,7 +3445,7 @@ export class Cline {
 		commitHash: string
 		mode: "full" | "checkpoint"
 	}) {
-		if (!this.enableCheckpoints) {
+		if (!this.checkpointService || !this.enableCheckpoints) {
 			return
 		}
 
@@ -3414,8 +3461,7 @@ export class Cline {
 		}
 
 		try {
-			const service = await this.getCheckpointService()
-			const changes = await service.getDiff({ from: previousCommitHash, to: commitHash })
+			const changes = await this.checkpointService.getDiff({ from: previousCommitHash, to: commitHash })
 
 			if (!changes?.length) {
 				vscode.window.showInformationMessage("No changes found.")
@@ -3441,30 +3487,13 @@ export class Cline {
 		}
 	}
 
-	public async checkpointSave({ isFirst }: { isFirst: boolean }) {
-		if (!this.enableCheckpoints) {
+	public checkpointSave() {
+		if (!this.checkpointService || !this.enableCheckpoints) {
 			return
 		}
 
-		try {
-			const service = await this.getCheckpointService()
-			const strategy = service.strategy
-			const version = service.version
-
-			const commit = await service.saveCheckpoint(`Task: ${this.taskId}, Time: ${Date.now()}`)
-			const fromHash = service.baseHash
-			const toHash = isFirst ? commit?.commit || fromHash : commit?.commit
-
-			if (toHash) {
-				await this.providerRef.deref()?.postMessageToWebview({ type: "currentCheckpointUpdated", text: toHash })
-
-				const checkpoint = { isFirst, from: fromHash, to: toHash, strategy, version }
-				await this.say("checkpoint_saved", toHash, undefined, undefined, checkpoint)
-			}
-		} catch (err) {
-			this.providerRef.deref()?.log("[checkpointSave] disabling checkpoints for this task")
-			this.enableCheckpoints = false
-		}
+		// Start the checkpoint process in the background.
+		this.checkpointService.saveCheckpoint(`Task: ${this.taskId}, Time: ${Date.now()}`)
 	}
 
 	public async checkpointRestore({
@@ -3476,7 +3505,7 @@ export class Cline {
 		commitHash: string
 		mode: "preview" | "restore"
 	}) {
-		if (!this.enableCheckpoints) {
+		if (!this.checkpointService || !this.enableCheckpoints) {
 			return
 		}
 
@@ -3487,8 +3516,7 @@ export class Cline {
 		}
 
 		try {
-			const service = await this.getCheckpointService()
-			await service.restoreCheckpoint(commitHash)
+			await this.checkpointService.restoreCheckpoint(commitHash)
 
 			await this.providerRef.deref()?.postMessageToWebview({ type: "currentCheckpointUpdated", text: commitHash })
 
diff --git a/src/services/checkpoints/CheckpointServiceFactory.ts b/src/services/checkpoints/CheckpointServiceFactory.ts
deleted file mode 100644
index ff39a1fe7e..0000000000
--- a/src/services/checkpoints/CheckpointServiceFactory.ts
+++ /dev/null
@@ -1,29 +0,0 @@
-import { LocalCheckpointService, LocalCheckpointServiceOptions } from "./LocalCheckpointService"
-import { ShadowCheckpointService, ShadowCheckpointServiceOptions } from "./ShadowCheckpointService"
-
-export type CreateCheckpointServiceFactoryOptions =
-	| {
-			strategy: "local"
-			options: LocalCheckpointServiceOptions
-	  }
-	| {
-			strategy: "shadow"
-			options: ShadowCheckpointServiceOptions
-	  }
-
-type CheckpointServiceType<T extends CreateCheckpointServiceFactoryOptions> = T extends { strategy: "local" }
-	? LocalCheckpointService
-	: T extends { strategy: "shadow" }
-		? ShadowCheckpointService
-		: never
-
-export class CheckpointServiceFactory {
-	public static create<T extends CreateCheckpointServiceFactoryOptions>(options: T): CheckpointServiceType<T> {
-		switch (options.strategy) {
-			case "local":
-				return LocalCheckpointService.create(options.options) as any
-			case "shadow":
-				return ShadowCheckpointService.create(options.options) as any
-		}
-	}
-}
diff --git a/src/services/checkpoints/LocalCheckpointService.ts b/src/services/checkpoints/LocalCheckpointService.ts
deleted file mode 100644
index ce5c6bd6ea..0000000000
--- a/src/services/checkpoints/LocalCheckpointService.ts
+++ /dev/null
@@ -1,440 +0,0 @@
-import fs from "fs/promises"
-import { existsSync } from "fs"
-import path from "path"
-
-import simpleGit, { SimpleGit, CleanOptions } from "simple-git"
-
-import { CheckpointStrategy, CheckpointService, CheckpointServiceOptions } from "./types"
-
-export interface LocalCheckpointServiceOptions extends CheckpointServiceOptions {}
-
-/**
- * The CheckpointService provides a mechanism for storing a snapshot of the
- * current VSCode workspace each time a Roo Code tool is executed. It uses Git
- * under the hood.
- *
- * HOW IT WORKS
- *
- * Two branches are used:
- *  - A main branch for normal operation (the branch you are currently on).
- *  - A hidden branch for storing checkpoints.
- *
- * Saving a checkpoint:
- *  - A temporary branch is created to store the current state.
- *  - All changes (including untracked files) are staged and committed on the temp branch.
- *  - The hidden branch is reset to match main.
- *  - The temporary branch commit is cherry-picked onto the hidden branch.
- *  - The workspace is restored to its original state and the temp branch is deleted.
- *
- * Restoring a checkpoint:
- *  - The workspace is restored to the state of the specified checkpoint using
- *    `git restore` and `git clean`.
- *
- * This approach allows for:
- *  - Non-destructive version control (main branch remains untouched).
- *  - Preservation of the full history of checkpoints.
- *  - Safe restoration to any previous checkpoint.
- *  - Atomic checkpoint operations with proper error recovery.
- *
- * NOTES
- *
- *  - Git must be installed.
- *  - If the current working directory is not a Git repository, we will
- *    initialize a new one with a .gitkeep file.
- *  - If you manually edit files and then restore a checkpoint, the changes
- *    will be lost. Addressing this adds some complexity to the implementation
- *    and it's not clear whether it's worth it.
- */
-
-export class LocalCheckpointService implements CheckpointService {
-	private static readonly USER_NAME = "Roo Code"
-	private static readonly USER_EMAIL = "support@roocode.com"
-	private static readonly CHECKPOINT_BRANCH = "roo-code-checkpoints"
-	private static readonly STASH_BRANCH = "roo-code-stash"
-
-	public readonly strategy: CheckpointStrategy = "local"
-	public readonly version = 1
-
-	public get baseHash() {
-		return this._baseHash
-	}
-
-	constructor(
-		public readonly taskId: string,
-		public readonly git: SimpleGit,
-		public readonly workspaceDir: string,
-		private readonly mainBranch: string,
-		private _baseHash: string,
-		private readonly hiddenBranch: string,
-		private readonly log: (message: string) => void,
-	) {}
-
-	private async ensureBranch(expectedBranch: string) {
-		const branch = await this.git.revparse(["--abbrev-ref", "HEAD"])
-
-		if (branch.trim() !== expectedBranch) {
-			throw new Error(`Git branch mismatch: expected '${expectedBranch}' but found '${branch}'`)
-		}
-	}
-
-	public async getDiff({ from, to }: { from?: string; to?: string }) {
-		const result = []
-
-		if (!from) {
-			from = this.baseHash
-		}
-
-		const { files } = await this.git.diffSummary([`${from}..${to}`])
-
-		for (const file of files.filter((f) => !f.binary)) {
-			const relPath = file.file
-			const absPath = path.join(this.workspaceDir, relPath)
-			const before = await this.git.show([`${from}:${relPath}`]).catch(() => "")
-
-			const after = to
-				? await this.git.show([`${to}:${relPath}`]).catch(() => "")
-				: await fs.readFile(absPath, "utf8").catch(() => "")
-
-			result.push({
-				paths: { relative: relPath, absolute: absPath },
-				content: { before, after },
-			})
-		}
-
-		return result
-	}
-
-	private async restoreMain({
-		branch,
-		stashSha,
-		force = false,
-	}: {
-		branch: string
-		stashSha: string
-		force?: boolean
-	}) {
-		let currentBranch = await this.git.revparse(["--abbrev-ref", "HEAD"])
-
-		if (currentBranch !== this.mainBranch) {
-			if (force) {
-				try {
-					await this.git.checkout(["-f", this.mainBranch])
-				} catch (err) {
-					this.log(
-						`[restoreMain] failed to force checkout ${this.mainBranch}: ${err instanceof Error ? err.message : String(err)}`,
-					)
-				}
-			} else {
-				try {
-					await this.git.checkout(this.mainBranch)
-				} catch (err) {
-					this.log(
-						`[restoreMain] failed to checkout ${this.mainBranch}: ${err instanceof Error ? err.message : String(err)}`,
-					)
-
-					// Escalate to a forced checkout if we can't checkout the
-					// main branch under normal circumstances.
-					currentBranch = await this.git.revparse(["--abbrev-ref", "HEAD"])
-
-					if (currentBranch !== this.mainBranch) {
-						await this.git.checkout(["-f", this.mainBranch]).catch(() => {})
-					}
-				}
-			}
-		}
-
-		currentBranch = await this.git.revparse(["--abbrev-ref", "HEAD"])
-
-		if (currentBranch !== this.mainBranch) {
-			throw new Error(`Unable to restore ${this.mainBranch}`)
-		}
-
-		if (stashSha) {
-			this.log(`[restoreMain] applying stash ${stashSha}`)
-
-			try {
-				await this.git.raw(["stash", "apply", "--index", stashSha])
-			} catch (err) {
-				this.log(`[restoreMain] Failed to apply stash: ${err instanceof Error ? err.message : String(err)}`)
-			}
-		}
-
-		this.log(`[restoreMain] restoring from ${branch} branch`)
-
-		try {
-			await this.git.raw(["restore", "--source", branch, "--worktree", "--", "."])
-		} catch (err) {
-			this.log(`[restoreMain] Failed to restore branch: ${err instanceof Error ? err.message : String(err)}`)
-		}
-	}
-
-	public async saveCheckpoint(message: string) {
-		const startTime = Date.now()
-
-		await this.ensureBranch(this.mainBranch)
-
-		const stashSha = (await this.git.raw(["stash", "create"])).trim()
-		const latestSha = await this.git.revparse([this.hiddenBranch])
-
-		/**
-		 * PHASE: Create stash
-		 * Mutations:
-		 *   - Create branch
-		 *   - Change branch
-		 */
-		const stashBranch = `${LocalCheckpointService.STASH_BRANCH}-${Date.now()}`
-		await this.git.checkout(["-b", stashBranch])
-		this.log(`[saveCheckpoint] created and checked out ${stashBranch}`)
-
-		/**
-		 * Phase: Stage stash
-		 * Mutations: None
-		 * Recovery:
-		 *   - UNDO: Create branch
-		 *   - UNDO: Change branch
-		 */
-		try {
-			await this.git.add(["-A"])
-		} catch (err) {
-			this.log(
-				`[saveCheckpoint] failed in stage stash phase: ${err instanceof Error ? err.message : String(err)}`,
-			)
-			await this.restoreMain({ branch: stashBranch, stashSha, force: true })
-			await this.git.branch(["-D", stashBranch]).catch(() => {})
-			throw err
-		}
-
-		/**
-		 * Phase: Commit stash
-		 * Mutations:
-		 *   - Commit stash
-		 *   - Change branch
-		 * Recovery:
-		 *   - UNDO: Create branch
-		 *   - UNDO: Change branch
-		 */
-		let stashCommit
-
-		try {
-			stashCommit = await this.git.commit(message, undefined, { "--no-verify": null })
-			this.log(`[saveCheckpoint] stashCommit: ${message} -> ${JSON.stringify(stashCommit)}`)
-		} catch (err) {
-			this.log(
-				`[saveCheckpoint] failed in stash commit phase: ${err instanceof Error ? err.message : String(err)}`,
-			)
-			await this.restoreMain({ branch: stashBranch, stashSha, force: true })
-			await this.git.branch(["-D", stashBranch]).catch(() => {})
-			throw err
-		}
-
-		if (!stashCommit) {
-			this.log("[saveCheckpoint] no stash commit")
-			await this.restoreMain({ branch: stashBranch, stashSha })
-			await this.git.branch(["-D", stashBranch])
-			return undefined
-		}
-
-		/**
-		 * PHASE: Diff
-		 * Mutations:
-		 *   - Checkout hidden branch
-		 * Recovery:
-		 *   - UNDO: Create branch
-		 *   - UNDO: Change branch
-		 *   - UNDO: Commit stash
-		 */
-		let diff
-
-		try {
-			diff = await this.git.diff([latestSha, stashBranch])
-		} catch (err) {
-			this.log(`[saveCheckpoint] failed in diff phase: ${err instanceof Error ? err.message : String(err)}`)
-			await this.restoreMain({ branch: stashBranch, stashSha, force: true })
-			await this.git.branch(["-D", stashBranch]).catch(() => {})
-			throw err
-		}
-
-		if (!diff) {
-			this.log("[saveCheckpoint] no diff")
-			await this.restoreMain({ branch: stashBranch, stashSha })
-			await this.git.branch(["-D", stashBranch])
-			return undefined
-		}
-
-		/**
-		 * PHASE: Reset
-		 * Mutations:
-		 *   - Reset hidden branch
-		 * Recovery:
-		 *   - UNDO: Create branch
-		 *   - UNDO: Change branch
-		 *   - UNDO: Commit stash
-		 */
-		try {
-			await this.git.checkout(this.hiddenBranch)
-			this.log(`[saveCheckpoint] checked out ${this.hiddenBranch}`)
-			await this.git.reset(["--hard", this.mainBranch])
-			this.log(`[saveCheckpoint] reset ${this.hiddenBranch}`)
-		} catch (err) {
-			this.log(`[saveCheckpoint] failed in reset phase: ${err instanceof Error ? err.message : String(err)}`)
-			await this.restoreMain({ branch: stashBranch, stashSha, force: true })
-			await this.git.branch(["-D", stashBranch]).catch(() => {})
-			throw err
-		}
-
-		/**
-		 * PHASE: Cherry pick
-		 * Mutations:
-		 *   - Hidden commit (NOTE: reset on hidden branch no longer needed in
-		 *     success scenario.)
-		 * Recovery:
-		 *   - UNDO: Create branch
-		 *   - UNDO: Change branch
-		 *   - UNDO: Commit stash
-		 *   - UNDO: Reset hidden branch
-		 */
-		let commit = ""
-
-		try {
-			try {
-				await this.git.raw(["cherry-pick", stashBranch])
-			} catch (err) {
-				// Check if we're in the middle of a cherry-pick.
-				// If the cherry-pick resulted in an empty commit (e.g., only
-				// deletions) then complete it with --allow-empty.
-				// Otherwise, rethrow the error.
-				if (existsSync(path.join(this.workspaceDir, ".git/CHERRY_PICK_HEAD"))) {
-					await this.git.raw(["commit", "--allow-empty", "--no-edit"])
-				} else {
-					throw err
-				}
-			}
-
-			commit = await this.git.revparse(["HEAD"])
-			this.log(`[saveCheckpoint] cherry-pick commit = ${commit}`)
-		} catch (err) {
-			this.log(
-				`[saveCheckpoint] failed in cherry pick phase: ${err instanceof Error ? err.message : String(err)}`,
-			)
-			await this.git.reset(["--hard", latestSha]).catch(() => {})
-			await this.restoreMain({ branch: stashBranch, stashSha, force: true })
-			await this.git.branch(["-D", stashBranch]).catch(() => {})
-			throw err
-		}
-
-		await this.restoreMain({ branch: stashBranch, stashSha })
-		await this.git.branch(["-D", stashBranch])
-
-		// We've gotten reports that checkpoints can be slow in some cases, so
-		// we'll log the duration of the checkpoint save.
-		const duration = Date.now() - startTime
-		this.log(`[saveCheckpoint] saved checkpoint ${commit} in ${duration}ms`)
-
-		return { commit }
-	}
-
-	public async restoreCheckpoint(commitHash: string) {
-		const startTime = Date.now()
-		await this.ensureBranch(this.mainBranch)
-		await this.git.clean([CleanOptions.FORCE, CleanOptions.RECURSIVE])
-		await this.git.raw(["restore", "--source", commitHash, "--worktree", "--", "."])
-		const duration = Date.now() - startTime
-		this.log(`[restoreCheckpoint] restored checkpoint ${commitHash} in ${duration}ms`)
-	}
-
-	public static async create({ taskId, workspaceDir, log = console.log }: LocalCheckpointServiceOptions) {
-		const git = simpleGit(workspaceDir)
-		const version = await git.version()
-
-		if (!version?.installed) {
-			throw new Error(`Git is not installed. Please install Git if you wish to use checkpoints.`)
-		}
-
-		if (!workspaceDir || !existsSync(workspaceDir)) {
-			throw new Error(`Base directory is not set or does not exist.`)
-		}
-
-		const { currentBranch, currentSha, hiddenBranch } = await LocalCheckpointService.initRepo(git, {
-			taskId,
-			workspaceDir,
-			log,
-		})
-
-		log(
-			`[create] taskId = ${taskId}, workspaceDir = ${workspaceDir}, currentBranch = ${currentBranch}, currentSha = ${currentSha}, hiddenBranch = ${hiddenBranch}`,
-		)
-
-		return new LocalCheckpointService(taskId, git, workspaceDir, currentBranch, currentSha, hiddenBranch, log)
-	}
-
-	private static async initRepo(
-		git: SimpleGit,
-		{ taskId, workspaceDir, log }: Required<LocalCheckpointServiceOptions>,
-	) {
-		const isExistingRepo = existsSync(path.join(workspaceDir, ".git"))
-
-		if (!isExistingRepo) {
-			await git.init()
-			log(`[initRepo] Initialized new Git repository at ${workspaceDir}`)
-		}
-
-		const globalUserName = await git.getConfig("user.name", "global")
-		const localUserName = await git.getConfig("user.name", "local")
-		const userName = localUserName.value || globalUserName.value
-
-		const globalUserEmail = await git.getConfig("user.email", "global")
-		const localUserEmail = await git.getConfig("user.email", "local")
-		const userEmail = localUserEmail.value || globalUserEmail.value
-
-		// Prior versions of this service indiscriminately set the local user
-		// config, and it should not override the global config. To address
-		// this we remove the local user config if it matches the default
-		// user name and email and there's a global config.
-		if (globalUserName.value && localUserName.value === LocalCheckpointService.USER_NAME) {
-			await git.raw(["config", "--unset", "--local", "user.name"])
-		}
-
-		if (globalUserEmail.value && localUserEmail.value === LocalCheckpointService.USER_EMAIL) {
-			await git.raw(["config", "--unset", "--local", "user.email"])
-		}
-
-		// Only set user config if not already configured.
-		if (!userName) {
-			await git.addConfig("user.name", LocalCheckpointService.USER_NAME)
-		}
-
-		if (!userEmail) {
-			await git.addConfig("user.email", LocalCheckpointService.USER_EMAIL)
-		}
-
-		if (!isExistingRepo) {
-			// We need at least one file to commit, otherwise the initial
-			// commit will fail, unless we use the `--allow-empty` flag.
-			// However, using an empty commit causes problems when restoring
-			// the checkpoint (i.e. the `git restore` command doesn't work
-			// for empty commits).
-			await fs.writeFile(path.join(workspaceDir, ".gitkeep"), "")
-			await git.add(".gitkeep")
-			const commit = await git.commit("Initial commit")
-
-			if (!commit.commit) {
-				throw new Error("Failed to create initial commit")
-			}
-
-			log(`[initRepo] Initial commit: ${commit.commit}`)
-		}
-
-		const currentBranch = await git.revparse(["--abbrev-ref", "HEAD"])
-		const currentSha = await git.revparse(["HEAD"])
-
-		const hiddenBranch = `${LocalCheckpointService.CHECKPOINT_BRANCH}-${taskId}`
-		const branchSummary = await git.branch()
-
-		if (!branchSummary.all.includes(hiddenBranch)) {
-			await git.checkoutBranch(hiddenBranch, currentBranch)
-			await git.checkout(currentBranch)
-		}
-
-		return { currentBranch, currentSha, hiddenBranch }
-	}
-}
diff --git a/src/services/checkpoints/ShadowCheckpointService.ts b/src/services/checkpoints/ShadowCheckpointService.ts
index 301602312e..70b3c68484 100644
--- a/src/services/checkpoints/ShadowCheckpointService.ts
+++ b/src/services/checkpoints/ShadowCheckpointService.ts
@@ -5,17 +5,18 @@ import { globby } from "globby"
 import simpleGit, { SimpleGit } from "simple-git"
 
 import { GIT_DISABLED_SUFFIX, GIT_EXCLUDES } from "./constants"
-import { CheckpointStrategy, CheckpointService, CheckpointServiceOptions } from "./types"
+import { CheckpointService, CheckpointServiceOptions, CheckpointEventEmitter } from "./types"
 
 export interface ShadowCheckpointServiceOptions extends CheckpointServiceOptions {
 	shadowDir: string
 }
 
-export class ShadowCheckpointService implements CheckpointService {
-	public readonly strategy: CheckpointStrategy = "shadow"
+export class ShadowCheckpointService extends CheckpointEventEmitter implements CheckpointService {
 	public readonly version = 1
 
+	private _checkpoints: string[] = []
 	private _baseHash?: string
+	private _isInitialized = false
 
 	public get baseHash() {
 		return this._baseHash
@@ -25,6 +26,18 @@ export class ShadowCheckpointService implements CheckpointService {
 		this._baseHash = value
 	}
 
+	public get isInitialized() {
+		return this._isInitialized
+	}
+
+	private set isInitialized(value: boolean) {
+		this._isInitialized = value
+	}
+
+	public get isDirty() {
+		return this._checkpoints.length > 0
+	}
+
 	private readonly shadowGitDir: string
 	private shadowGitConfigWorktree?: string
 
@@ -35,18 +48,26 @@ export class ShadowCheckpointService implements CheckpointService {
 		public readonly workspaceDir: string,
 		private readonly log: (message: string) => void,
 	) {
+		super()
 		this.shadowGitDir = path.join(this.shadowDir, "tasks", this.taskId, "checkpoints", ".git")
 	}
 
-	private async initShadowGit() {
+	public async initShadowGit() {
+		if (this.isInitialized) {
+			return
+		}
+
 		const fileExistsAtPath = (path: string) =>
 			fs
 				.access(path)
 				.then(() => true)
 				.catch(() => false)
 
+		let created = false
+		const startTime = Date.now()
+
 		if (await fileExistsAtPath(this.shadowGitDir)) {
-			this.log(`[initShadowGit] shadow git repo already exists at ${this.shadowGitDir}`)
+			this.log(`[CheckpointService#initShadowGit] shadow git repo already exists at ${this.shadowGitDir}`)
 			const worktree = await this.getShadowGitConfigWorktree()
 
 			if (worktree !== this.workspaceDir) {
@@ -57,7 +78,7 @@ export class ShadowCheckpointService implements CheckpointService {
 
 			this.baseHash = await this.git.revparse(["--abbrev-ref", "HEAD"])
 		} else {
-			this.log(`[initShadowGit] creating shadow git repo at ${this.workspaceDir}`)
+			this.log(`[CheckpointService#initShadowGit] creating shadow git repo at ${this.workspaceDir}`)
 
 			await this.git.init()
 			await this.git.addConfig("core.worktree", this.workspaceDir) // Sets the working tree to the current workspace.
@@ -78,7 +99,7 @@ export class ShadowCheckpointService implements CheckpointService {
 				}
 			} catch (error) {
 				this.log(
-					`[initShadowGit] failed to read .gitattributes: ${error instanceof Error ? error.message : String(error)}`,
+					`[CheckpointService#initShadowGit] failed to read .gitattributes: ${error instanceof Error ? error.message : String(error)}`,
 				)
 			}
 
@@ -93,8 +114,23 @@ export class ShadowCheckpointService implements CheckpointService {
 			await this.stageAll()
 			const { commit } = await this.git.commit("initial commit", { "--allow-empty": null })
 			this.baseHash = commit
-			this.log(`[initShadowGit] base commit is ${commit}`)
+			this.log(`[CheckpointService#initShadowGit] base commit is ${commit}`)
+
+			created = true
 		}
+
+		const duration = Date.now() - startTime
+		this.log(`[CheckpointService#initShadowGit] initialized shadow git in ${duration}ms`)
+
+		this.isInitialized = true
+
+		this.emit("initialize", {
+			type: "initialize",
+			workspaceDir: this.workspaceDir,
+			baseHash: this.baseHash,
+			created,
+			duration,
+		})
 	}
 
 	private async stageAll() {
@@ -103,7 +139,9 @@ export class ShadowCheckpointService implements CheckpointService {
 		try {
 			await this.git.add(".")
 		} catch (error) {
-			this.log(`[stageAll] failed to add files to git: ${error instanceof Error ? error.message : String(error)}`)
+			this.log(
+				`[CheckpointService#stageAll] failed to add files to git: ${error instanceof Error ? error.message : String(error)}`,
+			)
 		} finally {
 			await this.renameNestedGitRepos(false)
 		}
@@ -137,10 +175,12 @@ export class ShadowCheckpointService implements CheckpointService {
 
 			try {
 				await fs.rename(fullPath, newPath)
-				this.log(`${disable ? "disabled" : "enabled"} nested git repo ${gitPath}`)
+				this.log(
+					`[CheckpointService#renameNestedGitRepos] ${disable ? "disabled" : "enabled"} nested git repo ${gitPath}`,
+				)
 			} catch (error) {
 				this.log(
-					`failed to ${disable ? "disable" : "enable"} nested git repo ${gitPath}: ${error instanceof Error ? error.message : String(error)}`,
+					`[CheckpointService#renameNestedGitRepos] failed to ${disable ? "disable" : "enable"} nested git repo ${gitPath}: ${error instanceof Error ? error.message : String(error)}`,
 				)
 			}
 		}
@@ -152,7 +192,7 @@ export class ShadowCheckpointService implements CheckpointService {
 				this.shadowGitConfigWorktree = (await this.git.getConfig("core.worktree")).value || undefined
 			} catch (error) {
 				this.log(
-					`[getShadowGitConfigWorktree] failed to get core.worktree: ${error instanceof Error ? error.message : String(error)}`,
+					`[CheckpointService#getShadowGitConfigWorktree] failed to get core.worktree: ${error instanceof Error ? error.message : String(error)}`,
 				)
 			}
 		}
@@ -162,35 +202,63 @@ export class ShadowCheckpointService implements CheckpointService {
 
 	public async saveCheckpoint(message: string) {
 		try {
+			this.log("[CheckpointService#saveCheckpoint] starting checkpoint save")
+
+			if (!this.isInitialized) {
+				throw new Error("Shadow git repo not initialized")
+			}
+
 			const startTime = Date.now()
 			await this.stageAll()
 			const result = await this.git.commit(message)
-
-			if (result.commit) {
-				const duration = Date.now() - startTime
-				this.log(`[saveCheckpoint] saved checkpoint ${result.commit} in ${duration}ms`)
-				return result
-			} else {
-				return undefined
-			}
-		} catch (error) {
-			this.log(
-				`[saveCheckpoint] failed to create checkpoint: ${error instanceof Error ? error.message : String(error)}`,
-			)
-
+			const isFirst = this._checkpoints.length === 0
+			const fromHash = this._checkpoints[this._checkpoints.length - 1] ?? this.baseHash!
+			const toHash = result.commit ?? fromHash
+			this._checkpoints.push(toHash)
+			const duration = Date.now() - startTime
+			this.emit("checkpoint", { type: "checkpoint", isFirst, fromHash, toHash, duration })
+			return result.commit ? result : undefined
+		} catch (e) {
+			const error = e instanceof Error ? e : new Error(String(e))
+			this.log(`[CheckpointService#saveCheckpoint] failed to create checkpoint: ${error.message}`)
+			this.emit("error", { type: "error", error })
 			throw error
 		}
 	}
 
 	public async restoreCheckpoint(commitHash: string) {
-		const start = Date.now()
-		await this.git.clean("f", ["-d", "-f"])
-		await this.git.reset(["--hard", commitHash])
-		const duration = Date.now() - start
-		this.log(`[restoreCheckpoint] restored checkpoint ${commitHash} in ${duration}ms`)
+		try {
+			if (!this.isInitialized) {
+				throw new Error("Shadow git repo not initialized")
+			}
+
+			const start = Date.now()
+			await this.git.clean("f", ["-d", "-f"])
+			await this.git.reset(["--hard", commitHash])
+
+			// Remove all checkpoints after the specified commitHash.
+			const checkpointIndex = this._checkpoints.indexOf(commitHash)
+
+			if (checkpointIndex !== -1) {
+				this._checkpoints = this._checkpoints.slice(0, checkpointIndex + 1)
+			}
+
+			const duration = Date.now() - start
+			this.emit("restore", { type: "restore", commitHash, duration })
+			this.log(`[CheckpointService#restoreCheckpoint] restored checkpoint ${commitHash} in ${duration}ms`)
+		} catch (e) {
+			const error = e instanceof Error ? e : new Error(String(e))
+			this.log(`[CheckpointService#restoreCheckpoint] failed to restore checkpoint: ${error.message}`)
+			this.emit("error", { type: "error", error })
+			throw error
+		}
 	}
 
 	public async getDiff({ from, to }: { from?: string; to?: string }) {
+		if (!this.isInitialized) {
+			throw new Error("Shadow git repo not initialized")
+		}
+
 		const result = []
 
 		if (!from) {
@@ -223,6 +291,7 @@ export class ShadowCheckpointService implements CheckpointService {
 		try {
 			await simpleGit().version()
 		} catch (error) {
+			log("[CheckpointService#create] git is not installed")
 			throw new Error("Git must be installed to use checkpoints.")
 		}
 
@@ -241,9 +310,7 @@ export class ShadowCheckpointService implements CheckpointService {
 		const gitDir = path.join(checkpointsDir, ".git")
 		const git = simpleGit(path.dirname(gitDir))
 
-		log(`[create] taskId = ${taskId}, workspaceDir = ${workspaceDir}, shadowDir = ${shadowDir}`)
-		const service = new ShadowCheckpointService(taskId, git, shadowDir, workspaceDir, log)
-		await service.initShadowGit()
-		return service
+		log(`[CheckpointService#create] taskId = ${taskId}, workspaceDir = ${workspaceDir}, shadowDir = ${shadowDir}`)
+		return new ShadowCheckpointService(taskId, git, shadowDir, workspaceDir, log)
 	}
 }
diff --git a/src/services/checkpoints/__tests__/LocalCheckpointService.test.ts b/src/services/checkpoints/__tests__/LocalCheckpointService.test.ts
deleted file mode 100644
index 29ab7133a5..0000000000
--- a/src/services/checkpoints/__tests__/LocalCheckpointService.test.ts
+++ /dev/null
@@ -1,385 +0,0 @@
-// npx jest src/services/checkpoints/__tests__/LocalCheckpointService.test.ts
-
-import fs from "fs/promises"
-import path from "path"
-import os from "os"
-
-import { simpleGit, SimpleGit } from "simple-git"
-
-import { CheckpointServiceFactory } from "../CheckpointServiceFactory"
-import { LocalCheckpointService } from "../LocalCheckpointService"
-
-const tmpDir = path.join(os.tmpdir(), "test-LocalCheckpointService")
-
-describe("LocalCheckpointService", () => {
-	const taskId = "test-task"
-
-	let testFile: string
-	let service: LocalCheckpointService
-
-	const initRepo = async ({
-		workspaceDir,
-		userName = "Roo Code",
-		userEmail = "support@roocode.com",
-		testFileName = "test.txt",
-		textFileContent = "Hello, world!",
-	}: {
-		workspaceDir: string
-		userName?: string
-		userEmail?: string
-		testFileName?: string
-		textFileContent?: string
-	}) => {
-		// Create a temporary directory for testing.
-		await fs.mkdir(workspaceDir, { recursive: true })
-
-		// Initialize git repo.
-		const git = simpleGit(workspaceDir)
-		await git.init()
-		await git.addConfig("user.name", userName)
-		await git.addConfig("user.email", userEmail)
-
-		// Create test file.
-		const testFile = path.join(workspaceDir, testFileName)
-		await fs.writeFile(testFile, textFileContent)
-
-		// Create initial commit.
-		await git.add(".")
-		await git.commit("Initial commit")!
-
-		return { testFile }
-	}
-
-	beforeEach(async () => {
-		const workspaceDir = path.join(tmpDir, `checkpoint-service-test-${Date.now()}`)
-		const repo = await initRepo({ workspaceDir })
-
-		testFile = repo.testFile
-		service = await CheckpointServiceFactory.create({
-			strategy: "local",
-			options: { taskId, workspaceDir, log: () => {} },
-		})
-	})
-
-	afterEach(async () => {
-		jest.restoreAllMocks()
-	})
-
-	afterAll(async () => {
-		await fs.rm(tmpDir, { recursive: true, force: true })
-	})
-
-	describe("getDiff", () => {
-		it("returns the correct diff between commits", async () => {
-			await fs.writeFile(testFile, "Ahoy, world!")
-			const commit1 = await service.saveCheckpoint("First checkpoint")
-			expect(commit1?.commit).toBeTruthy()
-
-			await fs.writeFile(testFile, "Goodbye, world!")
-			const commit2 = await service.saveCheckpoint("Second checkpoint")
-			expect(commit2?.commit).toBeTruthy()
-
-			const diff1 = await service.getDiff({ to: commit1!.commit })
-			expect(diff1).toHaveLength(1)
-			expect(diff1[0].paths.relative).toBe("test.txt")
-			expect(diff1[0].paths.absolute).toBe(testFile)
-			expect(diff1[0].content.before).toBe("Hello, world!")
-			expect(diff1[0].content.after).toBe("Ahoy, world!")
-
-			const diff2 = await service.getDiff({ to: commit2!.commit })
-			expect(diff2).toHaveLength(1)
-			expect(diff2[0].paths.relative).toBe("test.txt")
-			expect(diff2[0].paths.absolute).toBe(testFile)
-			expect(diff2[0].content.before).toBe("Hello, world!")
-			expect(diff2[0].content.after).toBe("Goodbye, world!")
-
-			const diff12 = await service.getDiff({ from: commit1!.commit, to: commit2!.commit })
-			expect(diff12).toHaveLength(1)
-			expect(diff12[0].paths.relative).toBe("test.txt")
-			expect(diff12[0].paths.absolute).toBe(testFile)
-			expect(diff12[0].content.before).toBe("Ahoy, world!")
-			expect(diff12[0].content.after).toBe("Goodbye, world!")
-		})
-
-		it("handles new files in diff", async () => {
-			const newFile = path.join(service.workspaceDir, "new.txt")
-			await fs.writeFile(newFile, "New file content")
-			const commit = await service.saveCheckpoint("Add new file")
-			expect(commit?.commit).toBeTruthy()
-
-			const changes = await service.getDiff({ to: commit!.commit })
-			const change = changes.find((c) => c.paths.relative === "new.txt")
-			expect(change).toBeDefined()
-			expect(change?.content.before).toBe("")
-			expect(change?.content.after).toBe("New file content")
-		})
-
-		it("handles deleted files in diff", async () => {
-			const fileToDelete = path.join(service.workspaceDir, "new.txt")
-			await fs.writeFile(fileToDelete, "New file content")
-			const commit1 = await service.saveCheckpoint("Add file")
-			expect(commit1?.commit).toBeTruthy()
-
-			await fs.unlink(fileToDelete)
-			const commit2 = await service.saveCheckpoint("Delete file")
-			expect(commit2?.commit).toBeTruthy()
-
-			const changes = await service.getDiff({ from: commit1!.commit, to: commit2!.commit })
-			const change = changes.find((c) => c.paths.relative === "new.txt")
-			expect(change).toBeDefined()
-			expect(change!.content.before).toBe("New file content")
-			expect(change!.content.after).toBe("")
-		})
-	})
-
-	describe("saveCheckpoint", () => {
-		it("creates a checkpoint if there are pending changes", async () => {
-			await fs.writeFile(testFile, "Ahoy, world!")
-			const commit1 = await service.saveCheckpoint("First checkpoint")
-			expect(commit1?.commit).toBeTruthy()
-			const details1 = await service.git.show([commit1!.commit])
-			expect(details1).toContain("-Hello, world!")
-			expect(details1).toContain("+Ahoy, world!")
-
-			await fs.writeFile(testFile, "Hola, world!")
-			const commit2 = await service.saveCheckpoint("Second checkpoint")
-			expect(commit2?.commit).toBeTruthy()
-			const details2 = await service.git.show([commit2!.commit])
-			expect(details2).toContain("-Hello, world!")
-			expect(details2).toContain("+Hola, world!")
-
-			// Switch to checkpoint 1.
-			await service.restoreCheckpoint(commit1!.commit)
-			expect(await fs.readFile(testFile, "utf-8")).toBe("Ahoy, world!")
-
-			// Switch to checkpoint 2.
-			await service.restoreCheckpoint(commit2!.commit)
-			expect(await fs.readFile(testFile, "utf-8")).toBe("Hola, world!")
-
-			// Switch back to initial commit.
-			expect(service.baseHash).toBeTruthy()
-			await service.restoreCheckpoint(service.baseHash!)
-			expect(await fs.readFile(testFile, "utf-8")).toBe("Hello, world!")
-		})
-
-		it("preserves workspace and index state after saving checkpoint", async () => {
-			// Create three files with different states: staged, unstaged, and mixed.
-			const unstagedFile = path.join(service.workspaceDir, "unstaged.txt")
-			const stagedFile = path.join(service.workspaceDir, "staged.txt")
-			const mixedFile = path.join(service.workspaceDir, "mixed.txt")
-
-			await fs.writeFile(unstagedFile, "Initial unstaged")
-			await fs.writeFile(stagedFile, "Initial staged")
-			await fs.writeFile(mixedFile, "Initial mixed")
-			await service.git.add(["."])
-			const result = await service.git.commit("Add initial files")
-			expect(result?.commit).toBeTruthy()
-
-			await fs.writeFile(unstagedFile, "Modified unstaged")
-
-			await fs.writeFile(stagedFile, "Modified staged")
-			await service.git.add([stagedFile])
-
-			await fs.writeFile(mixedFile, "Modified mixed - staged")
-			await service.git.add([mixedFile])
-			await fs.writeFile(mixedFile, "Modified mixed - unstaged")
-
-			// Save checkpoint.
-			const commit = await service.saveCheckpoint("Test checkpoint")
-			expect(commit?.commit).toBeTruthy()
-
-			// Verify workspace state is preserved.
-			const status = await service.git.status()
-
-			// All files should be modified.
-			expect(status.modified).toContain("unstaged.txt")
-			expect(status.modified).toContain("staged.txt")
-			expect(status.modified).toContain("mixed.txt")
-
-			// Only staged and mixed files should be staged.
-			expect(status.staged).not.toContain("unstaged.txt")
-			expect(status.staged).toContain("staged.txt")
-			expect(status.staged).toContain("mixed.txt")
-
-			// Verify file contents.
-			expect(await fs.readFile(unstagedFile, "utf-8")).toBe("Modified unstaged")
-			expect(await fs.readFile(stagedFile, "utf-8")).toBe("Modified staged")
-			expect(await fs.readFile(mixedFile, "utf-8")).toBe("Modified mixed - unstaged")
-
-			// Verify staged changes (--cached shows only staged changes).
-			const stagedDiff = await service.git.diff(["--cached", "mixed.txt"])
-			expect(stagedDiff).toContain("-Initial mixed")
-			expect(stagedDiff).toContain("+Modified mixed - staged")
-
-			// Verify unstaged changes (shows working directory changes).
-			const unstagedDiff = await service.git.diff(["mixed.txt"])
-			expect(unstagedDiff).toContain("-Modified mixed - staged")
-			expect(unstagedDiff).toContain("+Modified mixed - unstaged")
-		})
-
-		it("does not create a checkpoint if there are no pending changes", async () => {
-			const commit0 = await service.saveCheckpoint("Zeroth checkpoint")
-			expect(commit0?.commit).toBeFalsy()
-
-			await fs.writeFile(testFile, "Ahoy, world!")
-			const commit1 = await service.saveCheckpoint("First checkpoint")
-			expect(commit1?.commit).toBeTruthy()
-
-			const commit2 = await service.saveCheckpoint("Second checkpoint")
-			expect(commit2?.commit).toBeFalsy()
-		})
-
-		it("includes untracked files in checkpoints", async () => {
-			// Create an untracked file.
-			const untrackedFile = path.join(service.workspaceDir, "untracked.txt")
-			await fs.writeFile(untrackedFile, "I am untracked!")
-
-			// Save a checkpoint with the untracked file.
-			const commit1 = await service.saveCheckpoint("Checkpoint with untracked file")
-			expect(commit1?.commit).toBeTruthy()
-
-			// Verify the untracked file was included in the checkpoint.
-			const details = await service.git.show([commit1!.commit])
-			expect(details).toContain("+I am untracked!")
-
-			// Create another checkpoint with a different state.
-			await fs.writeFile(testFile, "Changed tracked file")
-			const commit2 = await service.saveCheckpoint("Second checkpoint")
-			expect(commit2?.commit).toBeTruthy()
-
-			// Restore first checkpoint and verify untracked file is preserved.
-			await service.restoreCheckpoint(commit1!.commit)
-			expect(await fs.readFile(untrackedFile, "utf-8")).toBe("I am untracked!")
-			expect(await fs.readFile(testFile, "utf-8")).toBe("Hello, world!")
-
-			// Restore second checkpoint and verify untracked file remains (since
-			// restore preserves untracked files)
-			await service.restoreCheckpoint(commit2!.commit)
-			expect(await fs.readFile(untrackedFile, "utf-8")).toBe("I am untracked!")
-			expect(await fs.readFile(testFile, "utf-8")).toBe("Changed tracked file")
-		})
-
-		it("throws if we're on the wrong branch", async () => {
-			// Create and switch to a feature branch.
-			const currentBranch = await service.git.revparse(["--abbrev-ref", "HEAD"])
-			await service.git.checkoutBranch("feature", currentBranch)
-
-			// Attempt to save checkpoint from feature branch.
-			await expect(service.saveCheckpoint("test")).rejects.toThrow(
-				`Git branch mismatch: expected '${currentBranch}' but found 'feature'`,
-			)
-
-			// Attempt to restore checkpoint from feature branch.
-			expect(service.baseHash).toBeTruthy()
-
-			await expect(service.restoreCheckpoint(service.baseHash!)).rejects.toThrow(
-				`Git branch mismatch: expected '${currentBranch}' but found 'feature'`,
-			)
-		})
-
-		it("cleans up staged files if a commit fails", async () => {
-			await fs.writeFile(testFile, "Changed content")
-
-			// Mock git commit to simulate failure.
-			jest.spyOn(service.git, "commit").mockRejectedValue(new Error("Simulated commit failure"))
-
-			// Attempt to save checkpoint.
-			await expect(service.saveCheckpoint("test")).rejects.toThrow("Simulated commit failure")
-
-			// Verify files are unstaged.
-			const status = await service.git.status()
-			expect(status.staged).toHaveLength(0)
-		})
-
-		it("handles file deletions correctly", async () => {
-			await fs.writeFile(testFile, "I am tracked!")
-			const untrackedFile = path.join(service.workspaceDir, "new.txt")
-			await fs.writeFile(untrackedFile, "I am untracked!")
-			const commit1 = await service.saveCheckpoint("First checkpoint")
-			expect(commit1?.commit).toBeTruthy()
-
-			await fs.unlink(testFile)
-			await fs.unlink(untrackedFile)
-			const commit2 = await service.saveCheckpoint("Second checkpoint")
-			expect(commit2?.commit).toBeTruthy()
-
-			// Verify files are gone.
-			await expect(fs.readFile(testFile, "utf-8")).rejects.toThrow()
-			await expect(fs.readFile(untrackedFile, "utf-8")).rejects.toThrow()
-
-			// Restore first checkpoint.
-			await service.restoreCheckpoint(commit1!.commit)
-			expect(await fs.readFile(testFile, "utf-8")).toBe("I am tracked!")
-			expect(await fs.readFile(untrackedFile, "utf-8")).toBe("I am untracked!")
-
-			// Restore second checkpoint.
-			await service.restoreCheckpoint(commit2!.commit)
-			await expect(fs.readFile(testFile, "utf-8")).rejects.toThrow()
-			await expect(fs.readFile(untrackedFile, "utf-8")).rejects.toThrow()
-		})
-	})
-
-	describe("create", () => {
-		it("initializes a git repository if one does not already exist", async () => {
-			const workspaceDir = path.join(tmpDir, `checkpoint-service-test2-${Date.now()}`)
-			await fs.mkdir(workspaceDir)
-			const newTestFile = path.join(workspaceDir, "test.txt")
-			await fs.writeFile(newTestFile, "Hello, world!")
-
-			// Ensure the git repository was initialized.
-			const gitDir = path.join(workspaceDir, ".git")
-			await expect(fs.stat(gitDir)).rejects.toThrow()
-			const newService = await LocalCheckpointService.create({ taskId, workspaceDir, log: () => {} })
-			expect(await fs.stat(gitDir)).toBeTruthy()
-
-			// Save a checkpoint: Hello, world!
-			const commit1 = await newService.saveCheckpoint("Hello, world!")
-			expect(commit1?.commit).toBeTruthy()
-			expect(await fs.readFile(newTestFile, "utf-8")).toBe("Hello, world!")
-
-			// Restore initial commit; the file should no longer exist.
-			expect(newService.baseHash).toBeTruthy()
-			await newService.restoreCheckpoint(newService.baseHash!)
-			await expect(fs.access(newTestFile)).rejects.toThrow()
-
-			// Restore to checkpoint 1; the file should now exist.
-			await newService.restoreCheckpoint(commit1!.commit)
-			expect(await fs.readFile(newTestFile, "utf-8")).toBe("Hello, world!")
-
-			// Save a new checkpoint: Ahoy, world!
-			await fs.writeFile(newTestFile, "Ahoy, world!")
-			const commit2 = await newService.saveCheckpoint("Ahoy, world!")
-			expect(commit2?.commit).toBeTruthy()
-			expect(await fs.readFile(newTestFile, "utf-8")).toBe("Ahoy, world!")
-
-			// Restore "Hello, world!"
-			await newService.restoreCheckpoint(commit1!.commit)
-			expect(await fs.readFile(newTestFile, "utf-8")).toBe("Hello, world!")
-
-			// Restore "Ahoy, world!"
-			await newService.restoreCheckpoint(commit2!.commit)
-			expect(await fs.readFile(newTestFile, "utf-8")).toBe("Ahoy, world!")
-
-			// Restore initial commit.
-			expect(newService.baseHash).toBeTruthy()
-			await newService.restoreCheckpoint(newService.baseHash!)
-			await expect(fs.access(newTestFile)).rejects.toThrow()
-
-			await fs.rm(newService.workspaceDir, { recursive: true, force: true })
-		})
-
-		it("respects existing git user configuration", async () => {
-			const workspaceDir = path.join(tmpDir, `checkpoint-service-test-config2-${Date.now()}`)
-			const userName = "Custom User"
-			const userEmail = "custom@example.com"
-			await initRepo({ workspaceDir, userName, userEmail })
-
-			const newService = await LocalCheckpointService.create({ taskId, workspaceDir, log: () => {} })
-
-			expect((await newService.git.getConfig("user.name")).value).toBe(userName)
-			expect((await newService.git.getConfig("user.email")).value).toBe(userEmail)
-
-			await fs.rm(workspaceDir, { recursive: true, force: true })
-		})
-	})
-})
diff --git a/src/services/checkpoints/__tests__/ShadowCheckpointService.test.ts b/src/services/checkpoints/__tests__/ShadowCheckpointService.test.ts
index 5bcc5d444c..138e1130e8 100644
--- a/src/services/checkpoints/__tests__/ShadowCheckpointService.test.ts
+++ b/src/services/checkpoints/__tests__/ShadowCheckpointService.test.ts
@@ -3,11 +3,11 @@
 import fs from "fs/promises"
 import path from "path"
 import os from "os"
+import { EventEmitter } from "events"
 
 import { simpleGit, SimpleGit } from "simple-git"
 
 import { ShadowCheckpointService } from "../ShadowCheckpointService"
-import { CheckpointServiceFactory } from "../CheckpointServiceFactory"
 
 jest.mock("globby", () => ({
 	globby: jest.fn().mockResolvedValue([]),
@@ -63,13 +63,10 @@ describe("ShadowCheckpointService", () => {
 		const repo = await initRepo({ workspaceDir })
 
 		testFile = repo.testFile
-
-		service = await CheckpointServiceFactory.create({
-			strategy: "shadow",
-			options: { taskId, shadowDir, workspaceDir, log: () => {} },
-		})
-
 		workspaceGit = repo.git
+
+		service = await ShadowCheckpointService.create({ taskId, shadowDir, workspaceDir, log: () => {} })
+		await service.initShadowGit()
 	})
 
 	afterEach(async () => {
@@ -313,6 +310,7 @@ describe("ShadowCheckpointService", () => {
 			const gitDir = path.join(shadowDir, "tasks", taskId, "checkpoints", ".git")
 			await expect(fs.stat(gitDir)).rejects.toThrow()
 			const newService = await ShadowCheckpointService.create({ taskId, shadowDir, workspaceDir, log: () => {} })
+			await newService.initShadowGit()
 			expect(await fs.stat(gitDir)).toBeTruthy()
 
 			// Save a new checkpoint: Ahoy, world!
@@ -333,4 +331,168 @@ describe("ShadowCheckpointService", () => {
 			await fs.rm(newService.workspaceDir, { recursive: true, force: true })
 		})
 	})
+
+	describe("events", () => {
+		it("emits initialize event when service is created", async () => {
+			const shadowDir = path.join(tmpDir, `shadow-event-test-${Date.now()}`)
+			const workspaceDir = path.join(tmpDir, `workspace-event-test-${Date.now()}`)
+			await fs.mkdir(workspaceDir, { recursive: true })
+
+			const newTestFile = path.join(workspaceDir, "test.txt")
+			await fs.writeFile(newTestFile, "Testing events!")
+
+			// Create a mock implementation of emit to track events.
+			const emitSpy = jest.spyOn(EventEmitter.prototype, "emit")
+
+			// Create the service - this will trigger the initialize event.
+			const newService = await ShadowCheckpointService.create({ taskId, shadowDir, workspaceDir, log: () => {} })
+			await newService.initShadowGit()
+
+			// Find the initialize event in the emit calls.
+			let initializeEvent = null
+
+			for (let i = 0; i < emitSpy.mock.calls.length; i++) {
+				const call = emitSpy.mock.calls[i]
+
+				if (call[0] === "initialize") {
+					initializeEvent = call[1]
+					break
+				}
+			}
+
+			// Restore the spy.
+			emitSpy.mockRestore()
+
+			// Verify the event was emitted with the correct data.
+			expect(initializeEvent).not.toBeNull()
+			expect(initializeEvent.type).toBe("initialize")
+			expect(initializeEvent.workspaceDir).toBe(workspaceDir)
+			expect(initializeEvent.baseHash).toBeTruthy()
+			expect(typeof initializeEvent.created).toBe("boolean")
+			expect(typeof initializeEvent.duration).toBe("number")
+
+			// Verify the event was emitted with the correct data.
+			expect(initializeEvent).not.toBeNull()
+			expect(initializeEvent.type).toBe("initialize")
+			expect(initializeEvent.workspaceDir).toBe(workspaceDir)
+			expect(initializeEvent.baseHash).toBeTruthy()
+			expect(typeof initializeEvent.created).toBe("boolean")
+			expect(typeof initializeEvent.duration).toBe("number")
+
+			// Clean up.
+			await fs.rm(shadowDir, { recursive: true, force: true })
+			await fs.rm(workspaceDir, { recursive: true, force: true })
+		})
+
+		it("emits checkpoint event when saving checkpoint", async () => {
+			const checkpointHandler = jest.fn()
+			service.on("checkpoint", checkpointHandler)
+
+			await fs.writeFile(testFile, "Changed content for checkpoint event test")
+			const result = await service.saveCheckpoint("Test checkpoint event")
+			expect(result?.commit).toBeDefined()
+
+			expect(checkpointHandler).toHaveBeenCalledTimes(1)
+			const eventData = checkpointHandler.mock.calls[0][0]
+			expect(eventData.type).toBe("checkpoint")
+			expect(eventData.toHash).toBeDefined()
+			expect(eventData.toHash).toBe(result!.commit)
+			expect(typeof eventData.duration).toBe("number")
+		})
+
+		it("emits restore event when restoring checkpoint", async () => {
+			// First create a checkpoint to restore.
+			await fs.writeFile(testFile, "Content for restore test")
+			const commit = await service.saveCheckpoint("Checkpoint for restore test")
+			expect(commit?.commit).toBeTruthy()
+
+			// Change the file again.
+			await fs.writeFile(testFile, "Changed after checkpoint")
+
+			// Setup restore event listener.
+			const restoreHandler = jest.fn()
+			service.on("restore", restoreHandler)
+
+			// Restore the checkpoint.
+			await service.restoreCheckpoint(commit!.commit)
+
+			// Verify the event was emitted.
+			expect(restoreHandler).toHaveBeenCalledTimes(1)
+			const eventData = restoreHandler.mock.calls[0][0]
+			expect(eventData.type).toBe("restore")
+			expect(eventData.commitHash).toBe(commit!.commit)
+			expect(typeof eventData.duration).toBe("number")
+
+			// Verify the file was actually restored.
+			expect(await fs.readFile(testFile, "utf-8")).toBe("Content for restore test")
+		})
+
+		it("emits error event when an error occurs", async () => {
+			const errorHandler = jest.fn()
+			service.on("error", errorHandler)
+
+			// Force an error by providing an invalid commit hash.
+			const invalidCommitHash = "invalid-commit-hash"
+
+			// Try to restore an invalid checkpoint.
+			try {
+				await service.restoreCheckpoint(invalidCommitHash)
+			} catch (error) {
+				// Expected to throw, we're testing the event emission.
+			}
+
+			// Verify the error event was emitted.
+			expect(errorHandler).toHaveBeenCalledTimes(1)
+			const eventData = errorHandler.mock.calls[0][0]
+			expect(eventData.type).toBe("error")
+			expect(eventData.error).toBeInstanceOf(Error)
+		})
+
+		it("supports multiple event listeners for the same event", async () => {
+			const checkpointHandler1 = jest.fn()
+			const checkpointHandler2 = jest.fn()
+
+			service.on("checkpoint", checkpointHandler1)
+			service.on("checkpoint", checkpointHandler2)
+
+			await fs.writeFile(testFile, "Content for multiple listeners test")
+			const result = await service.saveCheckpoint("Testing multiple listeners")
+
+			// Verify both handlers were called with the same event data.
+			expect(checkpointHandler1).toHaveBeenCalledTimes(1)
+			expect(checkpointHandler2).toHaveBeenCalledTimes(1)
+
+			const eventData1 = checkpointHandler1.mock.calls[0][0]
+			const eventData2 = checkpointHandler2.mock.calls[0][0]
+
+			expect(eventData1).toEqual(eventData2)
+			expect(eventData1.type).toBe("checkpoint")
+			expect(eventData1.toHash).toBe(result?.commit)
+		})
+
+		it("allows removing event listeners", async () => {
+			const checkpointHandler = jest.fn()
+
+			// Add the listener.
+			service.on("checkpoint", checkpointHandler)
+
+			// Make a change and save a checkpoint.
+			await fs.writeFile(testFile, "Content for remove listener test - part 1")
+			await service.saveCheckpoint("Testing listener - part 1")
+
+			// Verify handler was called.
+			expect(checkpointHandler).toHaveBeenCalledTimes(1)
+			checkpointHandler.mockClear()
+
+			// Remove the listener.
+			service.off("checkpoint", checkpointHandler)
+
+			// Make another change and save a checkpoint.
+			await fs.writeFile(testFile, "Content for remove listener test - part 2")
+			await service.saveCheckpoint("Testing listener - part 2")
+
+			// Verify handler was not called after being removed.
+			expect(checkpointHandler).not.toHaveBeenCalled()
+		})
+	})
 })
diff --git a/src/services/checkpoints/index.ts b/src/services/checkpoints/index.ts
deleted file mode 100644
index e62b6119ce..0000000000
--- a/src/services/checkpoints/index.ts
+++ /dev/null
@@ -1,2 +0,0 @@
-export * from "./types"
-export * from "./CheckpointServiceFactory"
diff --git a/src/services/checkpoints/types.ts b/src/services/checkpoints/types.ts
index 50843abbd3..3ae9457fe8 100644
--- a/src/services/checkpoints/types.ts
+++ b/src/services/checkpoints/types.ts
@@ -1,3 +1,4 @@
+import EventEmitter from "events"
 import { CommitResult } from "simple-git"
 
 export type CheckpointResult = Partial<CommitResult> & Pick<CommitResult, "commit">
@@ -13,15 +14,12 @@ export type CheckpointDiff = {
 	}
 }
 
-export type CheckpointStrategy = "local" | "shadow"
-
 export interface CheckpointService {
 	saveCheckpoint(message: string): Promise<CheckpointResult | undefined>
 	restoreCheckpoint(commit: string): Promise<void>
 	getDiff(range: { from?: string; to?: string }): Promise<CheckpointDiff[]>
 	workspaceDir: string
 	baseHash?: string
-	strategy: CheckpointStrategy
 	version: number
 }
 
@@ -30,3 +28,38 @@ export interface CheckpointServiceOptions {
 	workspaceDir: string
 	log?: (message: string) => void
 }
+
+/**
+ * EventEmitter
+ */
+
+export interface CheckpointEventMap {
+	initialize: { type: "initialize"; workspaceDir: string; baseHash: string; created: boolean; duration: number }
+	checkpoint: {
+		type: "checkpoint"
+		isFirst: boolean
+		fromHash: string
+		toHash: string
+		duration: number
+	}
+	restore: { type: "restore"; commitHash: string; duration: number }
+	error: { type: "error"; error: Error }
+}
+
+export class CheckpointEventEmitter extends EventEmitter {
+	override emit<K extends keyof CheckpointEventMap>(event: K, data: CheckpointEventMap[K]): boolean {
+		return super.emit(event, data)
+	}
+
+	override on<K extends keyof CheckpointEventMap>(event: K, listener: (data: CheckpointEventMap[K]) => void): this {
+		return super.on(event, listener)
+	}
+
+	override off<K extends keyof CheckpointEventMap>(event: K, listener: (data: CheckpointEventMap[K]) => void): this {
+		return super.off(event, listener)
+	}
+
+	override once<K extends keyof CheckpointEventMap>(event: K, listener: (data: CheckpointEventMap[K]) => void): this {
+		return super.once(event, listener)
+	}
+}
diff --git a/webview-ui/src/components/chat/checkpoints/CheckpointSaved.tsx b/webview-ui/src/components/chat/checkpoints/CheckpointSaved.tsx
index c15bbd102c..5d3475c4d0 100644
--- a/webview-ui/src/components/chat/checkpoints/CheckpointSaved.tsx
+++ b/webview-ui/src/components/chat/checkpoints/CheckpointSaved.tsx
@@ -3,8 +3,6 @@ import { useMemo } from "react"
 import { CheckpointMenu } from "./CheckpointMenu"
 import { checkpointSchema } from "./schema"
 
-const REQUIRED_VERSION = 1
-
 type CheckpointSavedProps = {
 	ts: number
 	commitHash: string
@@ -22,7 +20,7 @@ export const CheckpointSaved = ({ checkpoint, ...props }: CheckpointSavedProps)
 
 		const result = checkpointSchema.safeParse(checkpoint)
 
-		if (!result.success || result.data.version < REQUIRED_VERSION) {
+		if (!result.success) {
 			return undefined
 		}
 
diff --git a/webview-ui/src/components/chat/checkpoints/schema.ts b/webview-ui/src/components/chat/checkpoints/schema.ts
index 7f097966b8..4acd32a6ab 100644
--- a/webview-ui/src/components/chat/checkpoints/schema.ts
+++ b/webview-ui/src/components/chat/checkpoints/schema.ts
@@ -4,8 +4,6 @@ export const checkpointSchema = z.object({
 	isFirst: z.boolean(),
 	from: z.string(),
 	to: z.string(),
-	strategy: z.enum(["local", "shadow"]),
-	version: z.number(),
 })
 
 export type Checkpoint = z.infer<typeof checkpointSchema>