diff --git a/CHANGELOG.md b/CHANGELOG.md
index 2553c6f61a2bf22cdc2d69640c682d983d7e5237..aca13b7ec56f0726ccf0f85861c7319366576656 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -47,6 +47,7 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 * Test for miscellaneous *-too-long errors.
 * Test for [caosdb-server#263](https://gitlab.com/linkahead/linkahead-server/-/issues/263): Unexpected server error when attempting to retrieve internal ROLE
   entities.
+* Test for [caosdb-server#268](https://gitlab.com/linkahead/linkahead-server/-/issues/268): Unexpected Server Error when non-existent file shall be inserted.
 
 ### Changed (for changes in existing functionality)
 
diff --git a/tests/test_issues_server.py b/tests/test_issues_server.py
index 5d782d9acb52e016b8578bf2045610fa40a53f2b..763009c10acfcd6ce483bcdc24336140cc90dc65 100644
--- a/tests/test_issues_server.py
+++ b/tests/test_issues_server.py
@@ -1552,8 +1552,16 @@ def test_264_accents_and_umlauts():
 
 
 @pytest.mark.xfail(reason="https://gitlab.com/linkahead/linkahead-server/-/issues/266 🤯")
-def test_266():
+def test_266_emoji():
     """Emojis as payload"""
     rt = db.RecordType(name="A nice 🤯 RecordType").insert()
     assert rt.id > 0
     assert "🤯" in rt.name
+
+
+@pytest.mark.xfail(reason="https://gitlab.com/linkahead/linkahead-server/-/issues/268")
+def test_268_insert_nonexistent_file():
+    """`db.File(path='IDoNotExist').insert()` leads to an unexpected server error."""
+    with pytest.raises(TransactionError) as tre:
+        db.File(path='IDoNotExist').insert()
+    assert repr(tre) == "File does not exist: IDoNotExist"  # TODO Replace by proper string.