diff --git a/codecov_cli/services/staticanalysis/__init__.py b/codecov_cli/services/staticanalysis/__init__.py
index 95175ae8..7a9914a5 100644
--- a/codecov_cli/services/staticanalysis/__init__.py
+++ b/codecov_cli/services/staticanalysis/__init__.py
@@ -109,7 +109,14 @@ async def run_analysis_entrypoint(
                 for el in files_that_need_upload:
                     all_tasks.append(send_single_upload_put(client, all_data, el))
                     bar.update(1, all_data[el["filepath"]])
-                resps = await asyncio.gather(*all_tasks)
+                try:
+                    resps = await asyncio.gather(*all_tasks)
+                except asyncio.CancelledError:
+                    message = (
+                        "Unknown error cancelled the upload tasks.\n"
+                        + f"Uploaded {len(uploaded_files)}/{len(files_that_need_upload)} files successfully."
+                    )
+                    raise click.ClickException(message)
             for resp in resps:
                 if resp["succeeded"]:
                     uploaded_files.append(resp["filepath"])
diff --git a/tests/services/static_analysis/test_static_analysis_service.py b/tests/services/static_analysis/test_static_analysis_service.py
index fae25226..08876634 100644
--- a/tests/services/static_analysis/test_static_analysis_service.py
+++ b/tests/services/static_analysis/test_static_analysis_service.py
@@ -1,3 +1,4 @@
+from asyncio import CancelledError
 from pathlib import Path
 from unittest.mock import MagicMock
 
@@ -148,6 +149,76 @@ async def side_effect(*args, **kwargs):
             "raw_upload_location": "http://storage-url",
         }
 
+    @pytest.mark.asyncio
+    async def test_static_analysis_service_CancelledError(self, mocker):
+        mock_file_finder = mocker.patch(
+            "codecov_cli.services.staticanalysis.select_file_finder"
+        )
+        mock_send_upload_put = mocker.patch(
+            "codecov_cli.services.staticanalysis.send_single_upload_put"
+        )
+
+        async def side_effect(client, all_data, el):
+            if el["filepath"] == "samples/inputs/sample_001.py":
+                return {
+                    "status_code": 204,
+                    "filepath": el["filepath"],
+                    "succeeded": True,
+                }
+            raise CancelledError("Pretending something cancelled this task")
+
+        mock_send_upload_put.side_effect = side_effect
+
+        files_found = map(
+            lambda filename: FileAnalysisRequest(str(filename), Path(filename)),
+            [
+                "samples/inputs/sample_001.py",
+                "samples/inputs/sample_002.py",
+            ],
+        )
+        mock_file_finder.return_value.find_files = MagicMock(return_value=files_found)
+        with responses.RequestsMock() as rsps:
+            rsps.add(
+                responses.POST,
+                "https://api.codecov.io/staticanalysis/analyses",
+                json={
+                    "external_id": "externalid",
+                    "filepaths": [
+                        {
+                            "state": "created",
+                            "filepath": "samples/inputs/sample_001.py",
+                            "raw_upload_location": "http://storage-url-001",
+                        },
+                        {
+                            "state": "created",
+                            "filepath": "samples/inputs/sample_002.py",
+                            "raw_upload_location": "http://storage-url-002",
+                        },
+                    ],
+                },
+                status=200,
+                match=[
+                    matchers.header_matcher({"Authorization": "Repotoken STATIC_TOKEN"})
+                ],
+            )
+
+            with pytest.raises(click.ClickException) as exp:
+                await run_analysis_entrypoint(
+                    config={},
+                    folder=".",
+                    numberprocesses=1,
+                    pattern="*.py",
+                    token="STATIC_TOKEN",
+                    commit="COMMIT",
+                    should_force=False,
+                    folders_to_exclude=[],
+                    enterprise_url=None,
+                )
+        assert "Unknown error cancelled the upload tasks." in str(exp.value)
+        mock_file_finder.assert_called_with({})
+        mock_file_finder.return_value.find_files.assert_called()
+        assert mock_send_upload_put.call_count == 2
+
     @pytest.mark.asyncio
     async def test_send_single_upload_put_success(self, mocker):
         mock_client = MagicMock()