diff --git a/packages/syft-job/src/syft_job/submission.py b/packages/syft-job/src/syft_job/submission.py
index c682b726489..b40b8275d92 100644
--- a/packages/syft-job/src/syft_job/submission.py
+++ b/packages/syft-job/src/syft_job/submission.py
@@ -93,13 +93,17 @@ def _digest(
     skip: frozenset[str] = frozenset(),
 ) -> str:
     digest = hashlib.sha256()
+    # Sort on the posix string: WindowsPath sorts case-insensitively.
     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 path: path.relative_to(submission_dir).as_posix(),
     )
     for path in files:
         digest.update(path.relative_to(submission_dir).as_posix().encode())
diff --git a/packages/syft-job/tests/test_submission_hash.py b/packages/syft-job/tests/test_submission_hash.py
new file mode 100644
index 00000000000..0cbe548865b
--- /dev/null
+++ b/packages/syft-job/tests/test_submission_hash.py
@@ -0,0 +1,29 @@
+"""The submission hash must not depend on how the OS sorts paths.
+
+WindowsPath sorts case-insensitively and PosixPath case-sensitively, so a DS on
+Windows and a DO on Linux would feed files in a different order.
+"""
+
+import hashlib
+from pathlib import Path
+
+from syft_job.submission import code_hash
+
+
+def test_code_hash_orders_files_by_posix_path(tmp_path: Path):
+    files = {
+        "run.sh": b"python code/a.py\n",
+        "code/B.py": b"b\n",
+        "code/a.py": b"a\n",
+    }
+    for name, content in files.items():
+        (tmp_path / name).parent.mkdir(parents=True, exist_ok=True)
+        (tmp_path / name).write_bytes(content)
+
+    expected = hashlib.sha256()
+    for name in sorted(files):  # "code/B.py" < "code/a.py" < "run.sh"
+        expected.update(name.encode())
+        expected.update(b"\0")
+        expected.update(hashlib.sha256(files[name]).digest())
+
+    assert code_hash(tmp_path) == expected.hexdigest()