diff --git a/packages/syft-job/src/syft_job/client.py b/packages/syft-job/src/syft_job/client.py
index 47803d00afa..0d8630ce4a0 100644
--- a/packages/syft-job/src/syft_job/client.py
+++ b/packages/syft-job/src/syft_job/client.py
@@ -669,7 +669,7 @@ def _job_has_all_files(self, ref: JobRef) -> bool:
         submission_dir = self.manager.submission_dir(ref)
         declared = metadata.headers.get(SUBMISSION_HASH_HEADER)
         if declared:
-            return code_hash(submission_dir) == declared
+            return code_hash(submission_dir, as_sent=True) == declared
         return has_listed_files(submission_dir, metadata.files)
 
     def _request_has_all_files(self, ref: RequestRef) -> bool:
diff --git a/packages/syft-job/src/syft_job/submission.py b/packages/syft-job/src/syft_job/submission.py
index b69f8b89742..1cb8b3b8576 100644
--- a/packages/syft-job/src/syft_job/submission.py
+++ b/packages/syft-job/src/syft_job/submission.py
@@ -108,12 +108,15 @@ def _digest(
 ) -> str:
     digest = hashlib.sha256()
     files = sorted(
-        path
-        for path in submission_dir.rglob("*")
-        if path.is_file()
-        and not _is_skipped(relative := path.relative_to(submission_dir))
-        and (entries is None or relative.parts[0] in entries)
-        and relative.as_posix() not in skip
+        (
+            path
+            for path in submission_dir.rglob("*")
+            if path.is_file()
+            and not _is_skipped(relative := path.relative_to(submission_dir))
+            and (entries is None or relative.parts[0] in entries)
+            and relative.as_posix() not in skip
+        ),
+        key=lambda p: p.relative_to(submission_dir).as_posix(),
     )
     for path in files:
         content = _as_sent(path) if as_sent else path.read_bytes()