diff --git a/.changeset/heavy-eyes-own.md b/.changeset/heavy-eyes-own.md
new file mode 100644
index 000000000..4765ed51f
--- /dev/null
+++ b/.changeset/heavy-eyes-own.md
@@ -0,0 +1,5 @@
+---
+"@trigger.dev/cli": patch
+---
+
+[dev] Better handle errors when registering endpoint
diff --git a/.changeset/lucky-crews-matter.md b/.changeset/lucky-crews-matter.md
new file mode 100644
index 000000000..ef58a1d00
--- /dev/null
+++ b/.changeset/lucky-crews-matter.md
@@ -0,0 +1,5 @@
+---
+"@trigger.dev/sdk": patch
+---
+
+Fixed responses from the PING action to match expected schema
diff --git a/examples/nextjs-clerk/package.json b/examples/nextjs-clerk/package.json
index 0b0df7ce9..a0215a6ca 100644
--- a/examples/nextjs-clerk/package.json
+++ b/examples/nextjs-clerk/package.json
@@ -20,8 +20,8 @@
     "react-dom": "^18.2.0",
     "tailwindcss": "3.3.2",
     "typescript": "5.1.6",
-    "@trigger.dev/sdk": "^2.0.0-next.4",
-    "@trigger.dev/nextjs": "^1.0.0-next.5"
+    "@trigger.dev/sdk": "workspace:*",
+    "@trigger.dev/nextjs": "workspace:*"
   },
   "devDependencies": {
     "@trigger.dev/cli": "workspace:*"
diff --git a/examples/nextjs-clerk/src/app/api/trigger/route.ts b/examples/nextjs-clerk/src/app/api/trigger/route.ts
index bde606eec..f7f24556f 100644
--- a/examples/nextjs-clerk/src/app/api/trigger/route.ts
+++ b/examples/nextjs-clerk/src/app/api/trigger/route.ts
@@ -23,6 +23,4 @@ new Job(client, {
   },
 });
 
-export const { POST, dynamic } = createAppRoute(client, {
-  path: "/api/trigger",
-});
+export const { POST, dynamic } = createAppRoute(client);
diff --git a/examples/nextjs-clerk/src/middleware.ts b/examples/nextjs-clerk/src/middleware.ts
index 126a58657..3955aad55 100644
--- a/examples/nextjs-clerk/src/middleware.ts
+++ b/examples/nextjs-clerk/src/middleware.ts
@@ -1,6 +1,8 @@
 import { authMiddleware } from "@clerk/nextjs";
 
-export default authMiddleware();
+export default authMiddleware({
+  publicRoutes: ["/api/trigger"],
+});
 
 export const config = {
   matcher: ["/((?!.*\\..*|_next).*)", "/", "/(api|trpc)(.*)"],
diff --git a/examples/nextjs-clerk/tsconfig.json b/examples/nextjs-clerk/tsconfig.json
index 0c7555fa7..398a4ac1b 100644
--- a/examples/nextjs-clerk/tsconfig.json
+++ b/examples/nextjs-clerk/tsconfig.json
@@ -20,7 +20,27 @@
       }
     ],
     "paths": {
-      "@/*": ["./src/*"]
+      "@/*": ["./src/*"],
+      "@trigger.dev/sdk": ["../../packages/trigger-sdk/src/index"],
+      "@trigger.dev/sdk/*": ["../../packages/trigger-sdk/src/*"],
+      "@trigger.dev/nextjs": ["../../packages/nextjs/src/index"],
+      "@trigger.dev/nextjs/*": ["../../packages/nextjs/src/*"],
+      "@trigger.dev/internal": ["../../packages/internal/src/index"],
+      "@trigger.dev/internal/*": ["../../packages/internal/src/*"],
+      "@trigger.dev/integration-kit": [
+        "../../packages/integration-kit/src/index"
+      ],
+      "@trigger.dev/integration-kit/*": [
+        "../../packages/integration-kit/src/*"
+      ],
+      "@trigger.dev/github": ["../../integrations/github/src/index"],
+      "@trigger.dev/github/*": ["../../integrations/github/src/*"],
+      "@trigger.dev/slack": ["../../integrations/slack/src/index"],
+      "@trigger.dev/slack/*": ["../../integrations/slack/src/*"],
+      "@trigger.dev/openai": ["../../integrations/openai/src/index"],
+      "@trigger.dev/openai/*": ["../../integrations/openai/src/*"],
+      "@trigger.dev/resend": ["../../integrations/resend/src/index"],
+      "@trigger.dev/resend/*": ["../../integrations/resend/src/*"]
     }
   },
   "include": ["next-env.d.ts", "**/*.ts", "**/*.tsx", ".next/types/**/*.ts"],
diff --git a/packages/cli/src/commands/dev.ts b/packages/cli/src/commands/dev.ts
index 7485b23d2..9a6835f72 100644
--- a/packages/cli/src/commands/dev.ts
+++ b/packages/cli/src/commands/dev.ts
@@ -17,9 +17,6 @@ export const DevCommandOptionsSchema = z.object({
 const throttleTimeMs = 1000;
 
 const formattedDate = new Intl.DateTimeFormat("en", {
-  year: "numeric",
-  month: "short",
-  day: "numeric",
   hour: "numeric",
   minute: "numeric",
   second: "numeric",
@@ -42,7 +39,7 @@ export async function devCommand(path: string, anyOptions: any) {
     );
     process.exit(1);
   }
-  logger.success(`✔️ Detected valid Next.js project`);
+  logger.success(`✔️ [trigger.dev] Detected valid Next.js project`);
 
   // Read from package.json to get the endpointId
   const endpointId = await getEndpointIdFromPackageJson(resolvedPath);
@@ -52,40 +49,51 @@ export async function devCommand(path: string, anyOptions: any) {
     );
     process.exit(1);
   }
-  logger.success(`✔️ Detected TriggerClient id: ${endpointId}`);
+  logger.success(`✔️ [trigger.dev] Detected TriggerClient id: ${endpointId}`);
 
   // Read from .env.local to get the TRIGGER_API_KEY and TRIGGER_API_URL
-  const { apiKey, apiUrl } = await getTriggerApiDetails(
-    resolvedPath,
-    options.envFile
-  );
-  logger.success(`✔️ Found API Key in ${options.envFile} file`);
-  const apiClient = new TriggerApi(apiKey, apiUrl);
+  const { apiUrl } = await getTriggerApiDetails(resolvedPath, options.envFile);
+  logger.success(`✔️ [trigger.dev] Found API Key in ${options.envFile} file`);
 
   // Setup tunnel
-  const tunnelSpinner = ora(`🚇 Creating tunnel`).start();
-  const tunnelUrl = await createTunnel(options.port);
-  tunnelSpinner.succeed(`🚇 Created tunnel: ${tunnelUrl}`);
+  const endpointUrl = await resolveEndpointUrl(apiUrl, options.port);
 
-  const connectingSpinner = ora(`Connecting to Trigger.dev...`).start();
+  const connectingSpinner = ora(
+    `[trigger.dev] Connecting to Trigger.dev...`
+  ).start();
 
   //refresh function
   let attemptCount = 0;
   const refresh = async () => {
-    const result = await refreshEndpoint(apiClient, endpointId, tunnelUrl);
+    const refreshedEndpointId = await getEndpointIdFromPackageJson(
+      resolvedPath
+    );
+
+    // Read from .env.local to get the TRIGGER_API_KEY and TRIGGER_API_URL
+    const { apiKey, apiUrl } = await getTriggerApiDetails(
+      resolvedPath,
+      options.envFile
+    );
+
+    const apiClient = new TriggerApi(apiKey, apiUrl);
+
+    const result = await refreshEndpoint(
+      apiClient,
+      refreshedEndpointId ?? endpointId,
+      endpointUrl
+    );
     if (result.success) {
       attemptCount = 0;
-      connectingSpinner.stop();
-      logger.success(
-        `🔄 Updated your Jobs ${formattedDate.format(
-          new Date(result.data.updatedAt)
-        )}`
+      connectingSpinner.succeed(
+        `[trigger.dev] 🔄 Refreshed ${
+          refreshedEndpointId ?? endpointId
+        } ${formattedDate.format(new Date(result.data.updatedAt))}`
       );
     } else {
       attemptCount++;
 
-      if (attemptCount === 10) {
-        logger.error(`🚨 Failed to connect: ${result.error}`);
+      if (attemptCount === 10 || !result.retryable) {
+        connectingSpinner.fail(`🚨 Failed to connect: ${result.error}`);
         logger.info(`Will attempt again on the next file change…`);
         return;
       }
@@ -169,6 +177,21 @@ async function getTriggerApiDetails(path: string, envFile: string) {
   return { apiKey, apiUrl };
 }
 
+async function resolveEndpointUrl(apiUrl: string, port: number) {
+  const apiURL = new URL(apiUrl);
+
+  if (apiURL.hostname === "localhost") {
+    return `http://localhost:${port}`;
+  }
+
+  // Setup tunnel
+  const tunnelSpinner = ora(`🚇 Creating tunnel`).start();
+  const tunnelUrl = await createTunnel(port);
+  tunnelSpinner.succeed(`🚇 Created tunnel: ${tunnelUrl}`);
+
+  return tunnelUrl;
+}
+
 async function createTunnel(port: number) {
   try {
     return await ngrok.connect(port);
@@ -190,15 +213,23 @@ async function refreshEndpoint(
     });
 
     if (!response.ok) {
-      return { success: false as const, error: response.error };
+      return {
+        success: false as const,
+        error: response.error,
+        retryable: response.retryable,
+      };
     }
 
     return { success: true as const, data: response.data };
   } catch (e) {
     if (e instanceof Error) {
-      return { success: false as const, error: e.message };
+      return { success: false as const, error: e.message, retryable: true };
     } else {
-      return { success: false as const, error: "Unknown error" };
+      return {
+        success: false as const,
+        error: "Unknown error",
+        retryable: true,
+      };
     }
   }
 }
diff --git a/packages/cli/src/commands/init.ts b/packages/cli/src/commands/init.ts
index c76820007..3f195e9ca 100644
--- a/packages/cli/src/commands/init.ts
+++ b/packages/cli/src/commands/init.ts
@@ -139,7 +139,7 @@ async function printNextSteps(
   logger.info("Next steps:");
   logger.info(`   1. Run your Next.js project locally with 'npm run dev'`);
   logger.info(
-    `   2. Run 'npx @trigger.dev/cli dev' to watch for changes and automatically register Trigger.dev jobs`
+    `   2. Run 'npx @trigger.dev/cli@latest dev' to watch for changes and automatically register Trigger.dev jobs`
   );
   logger.info(`   3. View your jobs at ${projectUrl}`);
 
diff --git a/packages/cli/src/utils/triggerApi.ts b/packages/cli/src/utils/triggerApi.ts
index 94761a24f..e82d7d414 100644
--- a/packages/cli/src/utils/triggerApi.ts
+++ b/packages/cli/src/utils/triggerApi.ts
@@ -23,7 +23,9 @@ export type EndpointResponse =
       ok: true;
       data: EndpointData;
     }
-  | { ok: false; error: string };
+  | { ok: false; error: string; retryable: boolean };
+
+const RETRYABLE_PATTERN = /Could not connect to endpoint/i;
 
 const WhoamiResponseSchema = z.object({
   id: z.string(),
@@ -97,27 +99,31 @@ export class TriggerApi {
             ok: false,
             error:
               "An unknown issue occurred when registering with Trigger.dev",
+            retryable: true,
           };
         }
 
-        const parsedJson = z.object({ message: z.string() }).safeParse(rawJson);
+        const parsedJson = z.object({ error: z.string() }).safeParse(rawJson);
 
         if (!parsedJson.success) {
           return {
             ok: false,
             error:
               "An unknown issue occurred when registering with Trigger.dev",
+            retryable: true,
           };
         }
 
         return {
           ok: false,
-          error: parsedJson.data.message,
+          error: parsedJson.data.error,
+          retryable: RETRYABLE_PATTERN.test(parsedJson.data.error),
         };
       } else {
         return {
           ok: false,
           error: "An unknown issue occurred when registering with Trigger.dev",
+          retryable: true,
         };
       }
     }
diff --git a/packages/trigger-sdk/src/triggerClient.ts b/packages/trigger-sdk/src/triggerClient.ts
index 4dbdebad5..c1f390e72 100644
--- a/packages/trigger-sdk/src/triggerClient.ts
+++ b/packages/trigger-sdk/src/triggerClient.ts
@@ -160,7 +160,7 @@ export class TriggerClient {
             status: 200,
             body: {
               ok: false,
-              message: "Missing endpoint ID",
+              error: "Missing endpoint ID",
             },
           };
         }
@@ -170,7 +170,7 @@ export class TriggerClient {
             status: 200,
             body: {
               ok: false,
-              message: `Endpoint ID mismatch error. Expected ${this.id}, got ${endpointId}`,
+              error: `Endpoint ID mismatch error. Expected ${this.id}, got ${endpointId}`,
             },
           };
         }
diff --git a/pnpm-lock.yaml b/pnpm-lock.yaml
index b9c7fca7e..9471a74c8 100644
--- a/pnpm-lock.yaml
+++ b/pnpm-lock.yaml
@@ -462,8 +462,8 @@ importers:
     specifiers:
       '@clerk/nextjs': ^4.21.12
       '@trigger.dev/cli': workspace:*
-      '@trigger.dev/nextjs': ^1.0.0-next.5
-      '@trigger.dev/sdk': ^2.0.0-next.4
+      '@trigger.dev/nextjs': workspace:*
+      '@trigger.dev/sdk': workspace:*
       '@types/node': 20.3.2
       '@types/react': ^18.0.21
       '@types/react-dom': ^18.0.6
@@ -476,8 +476,8 @@ importers:
       typescript: 5.1.6
     dependencies:
       '@clerk/nextjs': 4.21.12_5v7kwk6wz2hvmegftnptprfjvm
-      '@trigger.dev/nextjs': 1.0.0-next.5_yuyr3hquo7tgjdmhxnzkuafg3m
-      '@trigger.dev/sdk': 2.0.0-next.5
+      '@trigger.dev/nextjs': link:../../packages/nextjs
+      '@trigger.dev/sdk': link:../../packages/trigger-sdk
       '@types/node': 20.3.2
       '@types/react': 18.0.26
       '@types/react-dom': 18.0.10
@@ -10694,46 +10694,6 @@ packages:
       react-dom: 18.2.0_react@18.2.0
     dev: false
 
-  /@trigger.dev/nextjs/1.0.0-next.5_yuyr3hquo7tgjdmhxnzkuafg3m:
-    resolution: {integrity: sha512-41/RvyfuR3cPDCKAAhWOJMNw3KgA9uho7vcg8Q0ri8NCObsvxbStpnb5lpvNsUVOTyB7qy3tHULVJhKANczQqQ==}
-    engines: {node: '>=18'}
-    peerDependencies:
-      '@trigger.dev/sdk': ^2.0.0-next.2
-      next: ^13.3.1
-    dependencies:
-      '@trigger.dev/sdk': 2.0.0-next.5
-      debug: 4.3.4
-      next: 13.4.7_biqbaboplfbrettd7655fr4n2y
-    transitivePeerDependencies:
-      - supports-color
-    dev: false
-
-  /@trigger.dev/sdk/2.0.0-next.5:
-    resolution: {integrity: sha512-ERnhWSiWSO1sOkKVZfFP+bmbDOtgyviahY7tVP/8LD0cJb/uz5zSufcqHRHhVCXU423u24tJcYYJcXKNyoSmHQ==}
-    engines: {node: '>=18'}
-    dependencies:
-      chalk: 5.2.0
-      debug: 4.3.4
-      evt: 2.4.13
-      get-caller-file: 2.0.5
-      git-remote-origin-url: 4.0.0
-      git-repo-info: 2.1.1
-      node-fetch: 2.6.11
-      slug: 6.1.0
-      terminal-link: 3.0.0
-      ulid: 2.3.0
-      uuid: 9.0.0
-      ws: 8.12.0
-      zod: 3.21.4
-      zod-error: 1.1.0
-      zod-to-json-schema: 3.20.2_zod@3.21.4
-    transitivePeerDependencies:
-      - bufferutil
-      - encoding
-      - supports-color
-      - utf-8-validate
-    dev: false
-
   /@tsconfig/node10/1.0.9:
     resolution: {integrity: sha512-jNsYVVxU8v5g43Erja32laIDHXeoNvFEpX33OK4d6hljo3jDhCBDhx5dhCCTMWUojscpAagGiRkBKxpdl9fxqA==}
 
@@ -25800,14 +25760,6 @@ packages:
       zod: 3.20.2
     dev: false
 
-  /zod-to-json-schema/3.20.2_zod@3.21.4:
-    resolution: {integrity: sha512-qka3UAXmVXD8z5SHkRU89UyHp8JHJW7zc8RQCpt7QloJOn6uijwkjUm8o+M/cF1IysmKc5gxac/QeDikaQMdzQ==}
-    peerDependencies:
-      zod: ^3.20.0
-    dependencies:
-      zod: 3.21.4
-    dev: false
-
   /zod/3.20.2:
     resolution: {integrity: sha512-1MzNQdAvO+54H+EaK5YpyEy0T+Ejo/7YLHS93G3RnYWh5gaotGHwGeN/ZO687qEDU2y4CdStQYXVHIgrUl5UVQ==}
     dev: false