diff --git a/tests/test_dms_coverage.py b/tests/test_dms_coverage.py
index d9e3a5c..3d25c9d 100644
--- a/tests/test_dms_coverage.py
+++ b/tests/test_dms_coverage.py
@@ -664,7 +664,7 @@ class TestSharedWithMeCoverage:
         for i in range(3):
             resp = await client.post(
                 "/api/v1/dms/files/upload",
-                files={"file": (f"shared_{i}.pdf", PDF_CONTENT, "application/pdf")},
+                files={"file": (f"shared_{i}.pdf", PDF_CONTENT + str(i).encode(), "application/pdf")},
                 headers=ORIGIN_HEADER,
             )
             fid = resp.json()["id"]