diff --git a/package.json b/package.json
index 38e2df495..4c657876e 100644
--- a/package.json
+++ b/package.json
@@ -9,7 +9,7 @@
 	"type": "module",
 	"scripts": {
 		"dev": "node scripts/start-dev.js",
-		"dev:simple": "concurrently \"cd server && bun dev\" \"cd server && bun workers:dev\" \"cd vite && bun dev\" \"cd shared && bun dev\"",
+		"dev:simple": "concurrently \"cd shared && bun dev:watch\" \"cd server && bun dev\" \"cd server && bun workers:dev\" \"cd vite && bun dev\"",
 		"vite:build": "bun -F @autumn/shared build && bun -F @autumn/vite build:bun",
 		"vite:start": "bun -F @autumn/vite start:bun",
 		"shared": "bun -F @autumn/shared build",
@@ -29,9 +29,7 @@
 		"docker:up:ci": "docker compose -f docker-compose.ci.yml up --build",
 		"build:all": "pnpm -F shared build && pnpm -F server prod:build && pnpm -F vite build",
 		"vite:build:bun": "bun -F @autumn/shared build && bun -F @autumn/vite build:bun",
-		"vite:start:bun": "bun -F @autumn/shared build && bun -F @autumn/vite start:bun",
-		"dev:bun": "concurrently \"cd server && bun run dev\" \"cd vite && bun run dev\" \"bun -F @autumn/shared dev:bun\"",
-		"build:all:bun": "bun run -F @autumn/shared build:bun && bun run -F @autumn/server prod:build:bun && bun run -F @autumn/vite build:bun"
+		"vite:start:bun": "bun -F @autumn/shared build && bun -F @autumn/vite start:bun"
 	},
 	"dependencies": {
 		"@wooorm/starry-night": "^3.8.0",
diff --git a/scripts/start-dev.js b/scripts/start-dev.js
index 46a1bccc5..7ed2ff58f 100644
--- a/scripts/start-dev.js
+++ b/scripts/start-dev.js
@@ -6,17 +6,41 @@ async function startDev() {
 		// Detect and set ports
 		const { vitePort, serverPort } = await detectAndSetPorts();
 
-		console.log("\n🚀 Starting development servers...\n");
+		// Step 1: Build shared package first (initial build)
+		console.log("\n📦 Building shared package...\n");
+		const buildShared = spawn("bun", ["run", "build"], {
+			cwd: "shared",
+			stdio: "inherit",
+			shell: true,
+		});
 
-		// Start concurrently with the detected ports
+		await new Promise((resolve, reject) => {
+			buildShared.on("close", (code) => {
+				if (code !== 0) {
+					reject(new Error(`Shared package build failed with code ${code}`));
+				} else {
+					resolve();
+				}
+			});
+			buildShared.on("error", reject);
+		});
+
+		console.log("\n✅ Shared package built successfully!\n");
+		console.log("🚀 Starting development servers in watch mode...\n");
+
+		// Step 2: Start server, workers, and vite first (they'll use the built shared package)
 		const concurrentlyCmd = spawn(
 			"bunx",
 			[
 				"concurrently",
-				`"cd shared && bun run build && bun tsc"`,
+				"-n",
+				"server,workers,vite,shared",
+				"-c",
+				"green,yellow,blue,cyan",
 				`"cd server && SERVER_PORT=${serverPort} bun dev"`,
 				`"cd server && bun workers:dev"`,
 				`"cd vite && VITE_PORT=${vitePort} bun dev"`,
+				`"cd shared && bun run dev:watch"`,
 			],
 			{
 				stdio: "inherit",
diff --git a/server/package.json b/server/package.json
index 019484528..da87af2de 100644
--- a/server/package.json
+++ b/server/package.json
@@ -7,8 +7,8 @@
 	"scripts": {
 		"email": "email dev -p 3001",
 		"start": "bun src/index.ts",
-		"dev": "cross-env NODE_ENV=development bunx nodemon -w ../shared/dist -w src --ext js,ts --exec bun src/index.ts --ignore scripts --ignore tests",
-		"workers:dev": "cross-env NODE_ENV=development bunx nodemon -w ../shared/dist -w src/workers.ts -w src/queue --ext js,ts --exec bun src/workers.ts --ignore scripts --ignore tests",
+		"dev": "cross-env NODE_ENV=development bunx nodemon -w ../shared/dist -w src --ext js,ts --ignore '../shared/dist/**/*.d.ts' --ignore scripts --ignore tests --exec bun src/index.ts",
+		"workers:dev": "cross-env NODE_ENV=development bunx nodemon -w ../shared/dist -w src/workers.ts -w src/queue --ext js,ts --ignore '../shared/dist/**/*.d.ts' --ignore scripts --ignore tests --exec bun src/workers.ts",
 		"workers": "bun src/workers.ts",
 		"cron": "bun src/cron.ts",
 		"check": "bun src/check.ts",
diff --git a/shared/package.json b/shared/package.json
index 4ef1b6d02..fb78f7306 100644
--- a/shared/package.json
+++ b/shared/package.json
@@ -16,6 +16,7 @@
 		"api": "bun api/openapi.ts",
 		"build": "tsc --emitDeclarationOnly --outDir dist && bun build ./index.ts --outdir dist --format esm --target bun --external zod",
 		"dev": "bunx nodemon --ext ts --ignore dist --exec \"tsc --emitDeclarationOnly --outDir dist && bun build ./index.ts --outdir dist --format esm --target bun --external zod\"",
+		"dev:watch": "bun scripts/watch.js",
 		"db:push": "bun db:generate && bun db:migrate",
 		"db:generate": "cross-env NODE_OPTIONS=\"--import tsx\" bunx drizzle-kit generate --config drizzle.config.ts",
 		"db:migrate": "cross-env NODE_OPTIONS=\"--import tsx\" bunx drizzle-kit migrate --config drizzle.config.ts",
diff --git a/shared/scripts/watch.js b/shared/scripts/watch.js
new file mode 100644
index 000000000..a80c4b629
--- /dev/null
+++ b/shared/scripts/watch.js
@@ -0,0 +1,88 @@
+import { spawn } from "node:child_process";
+import { watch } from "node:fs";
+import { dirname, resolve } from "node:path";
+import { fileURLToPath } from "node:url";
+
+const __dirname = resolve(dirname(fileURLToPath(import.meta.url)), "..");
+
+let isBuilding = false;
+let rebuildQueued = false;
+
+function runBuild() {
+	if (isBuilding) {
+		rebuildQueued = true;
+		return;
+	}
+
+	isBuilding = true;
+	console.log("\n📦 [shared] Rebuilding...");
+
+	const build = spawn(
+		"bun",
+		[
+			"build",
+			"./index.ts",
+			"--outdir",
+			"dist",
+			"--format",
+			"esm",
+			"--target",
+			"bun",
+			"--external",
+			"zod",
+		],
+		{
+			cwd: __dirname,
+			stdio: "inherit",
+			shell: true,
+		},
+	);
+
+	// Run tsc in parallel
+	const tsc = spawn("tsc", ["--emitDeclarationOnly", "--outDir", "dist"], {
+		cwd: __dirname,
+		stdio: "inherit",
+		shell: true,
+	});
+
+	Promise.all([
+		new Promise((resolve) => build.on("close", resolve)),
+		new Promise((resolve) => tsc.on("close", resolve)),
+	]).then(() => {
+		console.log("✅ [shared] Rebuild complete");
+		isBuilding = false;
+
+		if (rebuildQueued) {
+			rebuildQueued = false;
+			setTimeout(() => runBuild(), 100);
+		}
+	});
+}
+
+// Watch for changes (excluding dist directory)
+const watcher = watch(__dirname, { recursive: true }, (eventType, filename) => {
+	if (
+		!filename ||
+		filename.includes("dist/") ||
+		filename.includes("node_modules/") ||
+		filename.includes("scripts/") ||
+		!filename.endsWith(".ts")
+	) {
+		return;
+	}
+
+	console.log(`\n📝 [shared] Changed: ${filename}`);
+	runBuild();
+});
+
+console.log("👀 [shared] Watching for changes...");
+
+process.on("SIGINT", () => {
+	watcher.close();
+	process.exit(0);
+});
+
+process.on("SIGTERM", () => {
+	watcher.close();
+	process.exit(0);
+});