diff --git a/src/core/Cline.ts b/src/core/Cline.ts
index 58be39a11b..83cdabd466 100644
--- a/src/core/Cline.ts
+++ b/src/core/Cline.ts
@@ -143,7 +143,7 @@ export class Cline {
 		this.fuzzyMatchThreshold = fuzzyMatchThreshold ?? 1.0
 		this.providerRef = new WeakRef(provider)
 		this.diffViewProvider = new DiffViewProvider(cwd)
-		this.checkpointsEnabled = process.platform !== "win32" && !!enableCheckpoints
+		this.checkpointsEnabled = enableCheckpoints ?? false
 
 		if (historyItem) {
 			this.taskId = historyItem.id
@@ -3240,7 +3240,6 @@ export class Cline {
 			this.checkpointService = await CheckpointService.create({
 				taskId: this.taskId,
 				baseDir: vscode.workspace.workspaceFolders?.map((folder) => folder.uri.fsPath).at(0) ?? "",
-				log: (message) => this.providerRef.deref()?.log(message),
 			})
 		}
 
diff --git a/src/services/checkpoints/CheckpointService.ts b/src/services/checkpoints/CheckpointService.ts
index 871179d500..bf5a2d90d5 100644
--- a/src/services/checkpoints/CheckpointService.ts
+++ b/src/services/checkpoints/CheckpointService.ts
@@ -2,6 +2,7 @@ import fs from "fs/promises"
 import { existsSync } from "fs"
 import path from "path"
 
+import debug from "debug"
 import simpleGit, { SimpleGit, CleanOptions } from "simple-git"
 
 export type CheckpointServiceOptions = {
@@ -312,11 +313,15 @@ export class CheckpointService {
 	}
 
 	public static async create({ taskId, git, baseDir, log = console.log }: CheckpointServiceOptions) {
-		if (process.platform === "win32") {
-			throw new Error("Checkpoints are not supported on Windows.")
-		}
-
-		git = git || simpleGit({ baseDir })
+		git =
+			git ||
+			simpleGit({
+				baseDir,
+				binary: "git",
+				maxConcurrentProcesses: 1,
+				config: [],
+				trimmed: true,
+			})
 
 		const version = await git.version()
 
diff --git a/src/services/checkpoints/__tests__/CheckpointService.test.ts b/src/services/checkpoints/__tests__/CheckpointService.test.ts
index caa0952fa1..9165da332a 100644
--- a/src/services/checkpoints/__tests__/CheckpointService.test.ts
+++ b/src/services/checkpoints/__tests__/CheckpointService.test.ts
@@ -14,7 +14,6 @@ describe("CheckpointService", () => {
 	let git: SimpleGit
 	let testFile: string
 	let service: CheckpointService
-	let originalPlatform: string
 
 	const initRepo = async ({
 		baseDir,
@@ -49,19 +48,6 @@ describe("CheckpointService", () => {
 		return { git, testFile }
 	}
 
-	beforeAll(() => {
-		originalPlatform = process.platform
-		Object.defineProperty(process, "platform", {
-			value: "darwin",
-		})
-	})
-
-	afterAll(() => {
-		Object.defineProperty(process, "platform", {
-			value: originalPlatform,
-		})
-	})
-
 	beforeEach(async () => {
 		const baseDir = path.join(os.tmpdir(), `checkpoint-service-test-${Date.now()}`)
 		const repo = await initRepo({ baseDir })
diff --git a/webview-ui/src/components/settings/SettingsView.tsx b/webview-ui/src/components/settings/SettingsView.tsx
index c60bbfd136..307ac250da 100644
--- a/webview-ui/src/components/settings/SettingsView.tsx
+++ b/webview-ui/src/components/settings/SettingsView.tsx
@@ -701,29 +701,27 @@ const SettingsView = ({ onDone }: SettingsViewProps) => {
 							</div>
 						)}
 
-						{process.platform !== "win32" && (
-							<div style={{ marginBottom: 15 }}>
-								<div style={{ display: "flex", alignItems: "center", gap: "5px" }}>
-									<span style={{ color: "var(--vscode-errorForeground)" }}>⚠️</span>
-									<VSCodeCheckbox
-										checked={checkpointsEnabled}
-										onChange={(e: any) => {
-											setCheckpointsEnabled(e.target.checked)
-										}}>
-										<span style={{ fontWeight: "500" }}>Enable experimental checkpoints</span>
-									</VSCodeCheckbox>
-								</div>
-								<p
-									style={{
-										fontSize: "12px",
-										marginTop: "5px",
-										color: "var(--vscode-descriptionForeground)",
+						<div style={{ marginBottom: 15 }}>
+							<div style={{ display: "flex", alignItems: "center", gap: "5px" }}>
+								<span style={{ color: "var(--vscode-errorForeground)" }}>⚠️</span>
+								<VSCodeCheckbox
+									checked={checkpointsEnabled}
+									onChange={(e: any) => {
+										setCheckpointsEnabled(e.target.checked)
 									}}>
-									When enabled, Roo will save a checkpoint whenever a file in the workspace is
-									modified, added or deleted, letting you easily revert to a previous state.
-								</p>
+									<span style={{ fontWeight: "500" }}>Enable experimental checkpoints</span>
+								</VSCodeCheckbox>
 							</div>
-						)}
+							<p
+								style={{
+									fontSize: "12px",
+									marginTop: "5px",
+									color: "var(--vscode-descriptionForeground)",
+								}}>
+								When enabled, Roo will save a checkpoint whenever a file in the workspace is modified,
+								added or deleted, letting you easily revert to a previous state.
+							</p>
+						</div>
 
 						{Object.entries(experimentConfigsMap)
 							.filter((config) => config[0] !== "DIFF_STRATEGY")