diff --git a/.changeset/twelve-actors-hide.md b/.changeset/twelve-actors-hide.md
new file mode 100644
index 0000000000..7187b92ab0
--- /dev/null
+++ b/.changeset/twelve-actors-hide.md
@@ -0,0 +1,5 @@
+---
+"trigger.dev": patch
+---
+
+Fix init.ts auto-import for deployed workers
diff --git a/packages/cli-v3/src/build/buildWorker.ts b/packages/cli-v3/src/build/buildWorker.ts
index 8c6e2d1cc3..583a9d2d82 100644
--- a/packages/cli-v3/src/build/buildWorker.ts
+++ b/packages/cli-v3/src/build/buildWorker.ts
@@ -116,6 +116,9 @@ export function rewriteBuildManifestPaths(
     loaderEntryPoint: buildManifest.loaderEntryPoint
       ? rewriteOutputPath(destinationDir, buildManifest.loaderEntryPoint)
       : undefined,
+    initEntryPoint: buildManifest.initEntryPoint
+      ? rewriteOutputPath(destinationDir, buildManifest.initEntryPoint)
+      : undefined,
   };
 }
 // Remove any query parameters from the entry path
diff --git a/packages/cli-v3/src/entryPoints/dev-run-worker.ts b/packages/cli-v3/src/entryPoints/dev-run-worker.ts
index 650143118b..66ed02d0db 100644
--- a/packages/cli-v3/src/entryPoints/dev-run-worker.ts
+++ b/packages/cli-v3/src/entryPoints/dev-run-worker.ts
@@ -104,12 +104,12 @@ const heartbeatIntervalMs = getEnvVar("HEARTBEAT_INTERVAL_MS");
 const standardLocalsManager = new StandardLocalsManager();
 localsAPI.setGlobalLocalsManager(standardLocalsManager);
 
-const standardRunTimelineMetricsManager = new StandardRunTimelineMetricsManager();
-runTimelineMetrics.setGlobalManager(standardRunTimelineMetricsManager);
-
 const standardLifecycleHooksManager = new StandardLifecycleHooksManager();
 lifecycleHooks.setGlobalLifecycleHooksManager(standardLifecycleHooksManager);
 
+const standardRunTimelineMetricsManager = new StandardRunTimelineMetricsManager();
+runTimelineMetrics.setGlobalManager(standardRunTimelineMetricsManager);
+
 const devUsageManager = new DevUsageManager();
 usage.setGlobalUsageManager(devUsageManager);
 timeout.setGlobalManager(new UsageTimeoutManager(devUsageManager));
diff --git a/packages/cli-v3/src/entryPoints/managed-run-worker.ts b/packages/cli-v3/src/entryPoints/managed-run-worker.ts
index 9e84130124..d1dc76a27b 100644
--- a/packages/cli-v3/src/entryPoints/managed-run-worker.ts
+++ b/packages/cli-v3/src/entryPoints/managed-run-worker.ts
@@ -324,6 +324,18 @@ const zodIpc = new ZodIpcConnection({
             async () => {
               const beforeImport = performance.now();
               resourceCatalog.setCurrentFileContext(taskManifest.entryPoint, taskManifest.filePath);
+
+              // Load init file if it exists
+              if (workerManifest.initEntryPoint) {
+                try {
+                  await import(normalizeImportPath(workerManifest.initEntryPoint));
+                  console.log(`Loaded init file from ${workerManifest.initEntryPoint}`);
+                } catch (err) {
+                  console.error(`Failed to load init file`, err);
+                  throw err;
+                }
+              }
+
               await import(normalizeImportPath(taskManifest.entryPoint));
               resourceCatalog.clearCurrentFileContext();
               const durationMs = performance.now() - beforeImport;
@@ -439,6 +451,8 @@ const zodIpc = new ZodIpcConnection({
             error: {
               type: "INTERNAL_ERROR",
               code: TaskRunErrorCodes.CONFIGURED_INCORRECTLY,
+              message: err instanceof Error ? err.message : String(err),
+              stackTrace: err instanceof Error ? err.stack : undefined,
             },
             usage: {
               durationMs: 0,
@@ -448,10 +462,7 @@ const zodIpc = new ZodIpcConnection({
         });
       }
     },
-    FLUSH: async ({ timeoutInMs }, sender) => {
-      await flushAll(timeoutInMs);
-    },
-    CANCEL: async ({ timeoutInMs }, sender) => {
+    CANCEL: async ({ timeoutInMs }) => {
       _isCancelled = true;
       cancelController.abort("run cancelled");
       await callCancelHooks(timeoutInMs);
@@ -460,6 +471,9 @@ const zodIpc = new ZodIpcConnection({
       }
       await flushAll(timeoutInMs);
     },
+    FLUSH: async ({ timeoutInMs }) => {
+      await flushAll(timeoutInMs);
+    },
     RESOLVE_WAITPOINT: async ({ waitpoint }) => {
       sharedWorkerRuntime.resolveWaitpoints([waitpoint]);
     },