diff --git a/.changeset/dev-session-store-dir.md b/.changeset/dev-session-store-dir.md
new file mode 100644
index 00000000000..81dbf444c2d
--- /dev/null
+++ b/.changeset/dev-session-store-dir.md
@@ -0,0 +1,5 @@
+---
+"trigger.dev": patch
+---
+
+Ensure the shared content-addressable store directory exists before writing so a second `trigger dev` session cannot crash after the previous session cleans it up.
diff --git a/packages/cli-v3/src/utilities/fileSystem.ts b/packages/cli-v3/src/utilities/fileSystem.ts
index d8632d96a75..ef8f6e07aa0 100644
--- a/packages/cli-v3/src/utilities/fileSystem.ts
+++ b/packages/cli-v3/src/utilities/fileSystem.ts
@@ -55,6 +55,10 @@ export async function createFileWithStore(
     await fsModule.unlink(filePath);
   }
 
+  // Ensure store directory exists. Concurrent `trigger dev` sessions share this
+  // path; the previous session's exit cleanup can delete it mid-build.
+  await fsModule.mkdir(storeDir, { recursive: true });
+
   // Check if content already exists in store by hash
   if (fsSync.existsSync(storePath)) {
     // Create hardlink from build path to store path