diff --git a/server/dive_server/crud.py b/server/dive_server/crud.py
index c9beef6fe..6c69a22e5 100644
--- a/server/dive_server/crud.py
+++ b/server/dive_server/crud.py
@@ -139,12 +139,11 @@ def get_data_by_type(
                 raise RestException('No array-type json objects are supported')
             if kwcoco.is_coco_json(data_dict):
                 as_type = FileType.COCO_JSON
+            elif models.MetadataMutable.is_dive_configuration(data_dict):
+                data_dict = models.MetadataMutable(**data_dict).dict(exclude_none=True)
+                as_type = FileType.DIVE_CONF
             else:
-                try:
-                    data_dict = models.MetadataMutable(**data_dict).dict(exclude_none=True)
-                    as_type = FileType.DIVE_CONF
-                except pydantic.ValidationError:
-                    as_type = FileType.DIVE_JSON
+                as_type = FileType.DIVE_JSON
         else:
             raise RestException('Got file of unknown and unusable type')
 
diff --git a/server/dive_utils/models.py b/server/dive_utils/models.py
index 0fd636fd5..32b189987 100644
--- a/server/dive_utils/models.py
+++ b/server/dive_utils/models.py
@@ -95,6 +95,19 @@ class MetadataMutable(BaseModel):
     confidenceFilters: Optional[Dict[str, float]]
     attributes: Optional[Dict[str, Attribute]]
 
+    @staticmethod
+    def is_dive_configuration(value: dict):
+        """
+        Check if value is a configuration file if at lease one of the config options is populated
+        """
+        keys = list(MetadataMutable.schema()['properties'].keys())
+
+        # Remove version: its appearance is not enough to indicate that
+        # the value is actually a configuration object.
+        keys.remove("version")
+
+        return any([value.get(key, False) for key in keys])
+
 
 class GirderMetadataStatic(MetadataMutable):
     # Required
diff --git a/server/tests/integration/test_dataset_download.py b/server/tests/integration/test_dataset_download.py
index 6758642b1..545e5e81c 100644
--- a/server/tests/integration/test_dataset_download.py
+++ b/server/tests/integration/test_dataset_download.py
@@ -36,3 +36,25 @@ def test_download_csv(user: dict):
                 if not row.startswith('#'):
                     track_set.add(row.split(',')[0])
             assert len(track_set) == expected[0]['trackCount']
+
+
+@pytest.mark.integration
+@pytest.mark.parametrize("user", users.values())
+@pytest.mark.run(order=7)
+def test_upload_json_detections(user: dict):
+    """
+    Upload new annotations, and verify that the existing annotations change.
+    This test cleans up after itself, and does not change the state of the system
+    for future tests
+    """
+    client = getClient(user['login'])
+    privateFolder = getTestFolder(client)
+    for dataset in client.listFolder(privateFolder['_id']):
+        old_tracks = client.get(f'dive_annotation?folderId={dataset["_id"]}')
+        newfile = client.uploadFileToFolder(dataset['_id'], '../testutils/tracks.json')
+        client.post(f'dive_rpc/postprocess/{dataset["_id"]}', data={"skipJobs": True})
+        new_tracks = client.get(f'dive_annotation?folderId={dataset["_id"]}')
+        assert '999999' not in old_tracks, "Tracks should have updated"
+        assert '999999' in new_tracks, "Should have one track, 999999"
+        assert len(new_tracks.keys()) == 1, "Should have a single track"
+        client.delete(f'item/{newfile["itemId"]}')  # Remove the uploaded detections
diff --git a/testutils/tracks.json b/testutils/tracks.json
new file mode 100644
index 000000000..eb1de7e4c
--- /dev/null
+++ b/testutils/tracks.json
@@ -0,0 +1 @@
+{"999999": {"begin": 0, "end": 0, "trackId": 0, "features": [{"frame": 0, "bounds": [670, 183, 968, 433], "interpolate": false, "keyframe": true}], "confidencePairs": [["motion_signature", 0.996269]], "attributes": {}}}