diff --git a/pi-extension.ts b/pi-extension.ts
index 5383734..dbf4ecf 100644
--- a/pi-extension.ts
+++ b/pi-extension.ts
@@ -78,7 +78,12 @@ export default function (pi: ExtensionAPI) {
 			try {
 				const targetPath = params.path || ctx.cwd;
 				const client = getPiLLMClient(ctx);
-				await initProject(targetPath, { verbose: false, llmClient: client, cacheDir: ctx.cwd });
+				await initProject(targetPath, {
+					verbose: false,
+					llmClient: client,
+					cacheDir: ctx.cwd,
+					onProgress: (msg) => _onUpdate?.({ content: [{ type: "text", text: msg }] }),
+				});
 				return {
 					content: [
 						{
@@ -199,7 +204,12 @@ export default function (pi: ExtensionAPI) {
 			try {
 				const targetPath = params.path || ctx.cwd;
 				const client = getPiLLMClient(ctx);
-				await reinitPath(targetPath, { verbose: false, llmClient: client, cacheDir: ctx.cwd });
+				await reinitPath(targetPath, {
+					verbose: false,
+					llmClient: client,
+					cacheDir: ctx.cwd,
+					onProgress: (msg) => _onUpdate?.({ content: [{ type: "text", text: msg }] }),
+				});
 				return {
 					content: [
 						{
diff --git a/src/init.ts b/src/init.ts
index a3f1f89..8eff58d 100644
--- a/src/init.ts
+++ b/src/init.ts
@@ -16,6 +16,7 @@ export interface InitOptions {
 	verbose?: boolean;
 	llmClient?: LLMClient;
 	cacheDir?: string;
+	onProgress?: (message: string) => void;
 }
 
 export async function initProject(
@@ -23,11 +24,15 @@ export async function initProject(
 	options: InitOptions = {},
 ): Promise<void> {
 	const entries = discoverProject(rootPath);
+	options.onProgress?.(`Scanning ${entries.length} directories...`);
 
-	for (const entry of entries) {
-		await generateDirectoryMap(entry, options.llmClient, options.cacheDir);
+	for (let i = 0; i < entries.length; i++) {
+		const entry = entries[i];
+		options.onProgress?.(`[${i + 1}/${entries.length}] Analyzing ${entry.relativePath} (${entry.files.length} files)...`);
+		await generateDirectoryMap(entry, options.llmClient, options.cacheDir, options.onProgress);
 	}
 
+	options.onProgress?.(`Generated ${entries.length} .pi-map.md files`);
 	if (options.verbose !== false) {
 		console.log(`Generated ${entries.length} .pi-map.md files`);
 	}
@@ -37,12 +42,14 @@ export async function generateDirectoryMap(
 	entry: DirectoryEntry,
 	llmClient?: LLMClient,
 	cacheDir?: string,
+	onProgress?: (message: string) => void,
 ): Promise<FileEntry[]> {
 	// Process files in parallel (4 concurrent) with retry logic
 	const fileData = await processFiles(
 		entry.files,
 		async (file) => {
 			const filePath = join(entry.dirPath, file);
+			onProgress?.(`  → ${file}`);
 			const llmData = await extractFileLLM(filePath, llmClient, cacheDir);
 			const astData = await extractFileAST(filePath);
 			return mergeFileData(file, llmData, astData);