diff --git a/.changeset/bundle-deterministic-file-order.md b/.changeset/bundle-deterministic-file-order.md
new file mode 100644
index 00000000000..d8e7a0ca264
--- /dev/null
+++ b/.changeset/bundle-deterministic-file-order.md
@@ -0,0 +1,5 @@
+---
+"trigger.dev": patch
+---
+
+Fix non-deterministic task-to-file attribution when multiple tasks share an output bundle. `Object.entries` iteration order is not guaranteed, so tasks defined in imported files could be attributed to the wrong source file. Files are now sorted by entry path before registration.
diff --git a/packages/cli-v3/src/build/bundle.ts b/packages/cli-v3/src/build/bundle.ts
index 4d1cfd53f86..a0197934a8a 100644
--- a/packages/cli-v3/src/build/bundle.ts
+++ b/packages/cli-v3/src/build/bundle.ts
@@ -307,6 +307,8 @@ export async function getBundleResultFromBuild(
     }
   }
 
+  files.sort((a, b) => a.entry.localeCompare(b.entry));
+
   if (!configPath) {
     return undefined;
   }