diff --git a/tests/test_issues_server.py b/tests/test_issues_server.py
index 2f4b5c524a0b96a48417fb67cd5acac1416411fe..d36a6b25ad6893731bff9816bb03ffc4e90077a0 100644
--- a/tests/test_issues_server.py
+++ b/tests/test_issues_server.py
@@ -24,6 +24,10 @@
 
 """Tests for issues on gitlab.com, project caosdb-server."""
 
+import os
+import tempfile
+import time
+
 import caosdb as db
 from caosdb.exceptions import EntityError, TransactionError
 import pytest
@@ -137,3 +141,27 @@ def test_issue_85_b():
     C.update()
     C.add_parent(A)
     C.update()  # Failed at this step
+
+
+def test_issue_99():
+    """Checksum updating failed with versioning enabled.
+    """
+
+    # Using files in extroot, because this allows us to update the file content from the outside.
+    local_dir = os.path.join(db.get_config().get("IntegrationTests",
+                                                 "test_files.test_insert_files_in_dir.local"),
+                             "test_issue_99")
+    docker_dir = os.path.join(db.get_config().get("IntegrationTests",
+                                                  "test_files.test_insert_files_in_dir.server"),
+                              "test_issue_99")
+    with tempfile.NamedTemporaryFile(dir=local_dir) as file_99:
+        # Create File entity in CaosDB
+        c = db.Container()
+        c.insert(unique=False, raise_exception_on_error=False,
+                 flags={"InsertFilesInDir": docker_dir})
+        dbfile = c[0]
+
+        # Checksum should exist after a short time
+        time.sleep(0.5)
+        dbfile.retrieve()
+        assert dbfile.checksum is not None