diff --git a/packages/cli/package.json b/packages/cli/package.json
index 25f14f1bb..63e8cbe72 100644
--- a/packages/cli/package.json
+++ b/packages/cli/package.json
@@ -55,6 +55,7 @@
   "dependencies": {
     "@types/degit": "^2.8.3",
     "chalk": "^5.2.0",
+    "chokidar": "^3.5.3",
     "commander": "^9.4.1",
     "degit": "^2.8.4",
     "execa": "^7.0.0",
diff --git a/packages/cli/src/commands/dev.ts b/packages/cli/src/commands/dev.ts
index fb27c322e..8e2ceacd4 100644
--- a/packages/cli/src/commands/dev.ts
+++ b/packages/cli/src/commands/dev.ts
@@ -6,6 +6,7 @@ import { resolvePath } from "../utils/parseNameAndPath.js";
 import ngrok from "ngrok";
 import { z } from "zod";
 import { TriggerApi } from "../utils/triggerApi.js";
+import chokidar from "chokidar";
 
 export const DevCommandOptionsSchema = z.object({
   port: z.coerce.number(),
@@ -13,6 +14,18 @@ export const DevCommandOptionsSchema = z.object({
   tunnel: z.union([z.literal("ngrok"), z.literal("localtunnel")]),
 });
 
+const compileTimeWaitMs = 300;
+const throttleTimeMs = 1000;
+
+const formattedDate = new Intl.DateTimeFormat("en", {
+  year: "numeric",
+  month: "short",
+  day: "numeric",
+  hour: "numeric",
+  minute: "numeric",
+  second: "numeric",
+});
+
 export async function devCommand(path: string, anyOptions: any) {
   const result = DevCommandOptionsSchema.safeParse(anyOptions);
   if (!result.success) {
@@ -54,16 +67,28 @@ export async function devCommand(path: string, anyOptions: any) {
   const tunnelUrl = await createTunnel(options.port);
   logger.success(`🚇 Created tunnel: ${tunnelUrl}`);
 
-  logger.info(`Connecting to Trigger.dev...`);
+  logger.info(`🔌 Connecting to Trigger.dev...`);
   //wait 200ms
   // await wait(200);
 
-  //do initial refresh of the endpoint
-  //todo get path for API
-  await refreshEndpoint(apiClient, endpointId, tunnelUrl);
-  logger.success(`🔄 Updated your Jobs`);
+  //refresh function
+  const refresh = async () => {
+    //compiling takes a bit of time
+    await wait(compileTimeWaitMs);
+    const result = await refreshEndpoint(apiClient, endpointId, tunnelUrl);
+    if (result?.updatedAt) {
+      logger.success(
+        `🔄 Updated your Jobs ${formattedDate.format(
+          new Date(result.updatedAt)
+        )}`
+      );
+    }
+  };
 
-  // Watch for changes to .ts files and call triggerApi.indexEndpoint
+  // Watch for changes to .ts files and refresh endpoints
+  chokidar.watch(resolvedPath).on("all", (event, path) => {
+    throttle(refresh, throttleTimeMs);
+  });
 }
 
 async function getEndpointIdFromPackageJson(path: string) {
@@ -139,3 +164,19 @@ async function refreshEndpoint(
 
   return response.data;
 }
+
+//wait function
+async function wait(ms: number) {
+  return new Promise((resolve) => {
+    setTimeout(resolve, ms);
+  });
+}
+
+//throttle function
+let throttleTimeout: NodeJS.Timeout | null = null;
+function throttle(fn: () => any, delay: number) {
+  if (throttleTimeout) {
+    clearTimeout(throttleTimeout);
+  }
+  throttleTimeout = setTimeout(fn, delay);
+}
diff --git a/pnpm-lock.yaml b/pnpm-lock.yaml
index 98c8efc4e..1f2d38d70 100644
--- a/pnpm-lock.yaml
+++ b/pnpm-lock.yaml
@@ -637,6 +637,7 @@ importers:
       '@types/node': '16'
       '@types/node-fetch': ^2.6.2
       chalk: ^5.2.0
+      chokidar: ^3.5.3
       commander: ^9.4.1
       degit: ^2.8.4
       execa: ^7.0.0
@@ -658,6 +659,7 @@ importers:
     dependencies:
       '@types/degit': 2.8.3
       chalk: 5.2.0
+      chokidar: 3.5.3
       commander: 9.5.0
       degit: 2.8.4
       execa: 7.0.0