diff --git a/src/fastapi_cloud_cli/commands/deploy.py b/src/fastapi_cloud_cli/commands/deploy.py
index 4daa885..9c95dab 100644
--- a/src/fastapi_cloud_cli/commands/deploy.py
+++ b/src/fastapi_cloud_cli/commands/deploy.py
@@ -32,6 +32,19 @@
 logger = logging.getLogger(__name__)
 
 
+def _cancel_upload(deployment_id: str) -> None:
+    logger.debug("Cancelling upload for deployment: %s", deployment_id)
+
+    try:
+        with APIClient() as client:
+            response = client.post(f"/deployments/{deployment_id}/upload-cancelled")
+            response.raise_for_status()
+
+            logger.debug("Upload cancellation notification sent successfully")
+    except Exception as e:
+        logger.debug("Failed to notify server about upload cancellation: %s", e)
+
+
 def _get_app_name(path: Path) -> str:
     # TODO: use pyproject.toml to get the app name
     return path.name
@@ -598,15 +611,19 @@ def deploy(
                 logger.debug("Creating deployment for app: %s", app.id)
                 deployment = _create_deployment(app.id)
 
-                progress.log(
-                    f"Deployment created successfully! Deployment slug: {deployment.slug}"
-                )
+                try:
+                    progress.log(
+                        f"Deployment created successfully! Deployment slug: {deployment.slug}"
+                    )
 
-                progress.log("Uploading deployment...")
+                    progress.log("Uploading deployment...")
 
-                _upload_deployment(deployment.id, archive_path)
+                    _upload_deployment(deployment.id, archive_path)
 
-                progress.log("Deployment uploaded successfully!")
+                    progress.log("Deployment uploaded successfully!")
+                except KeyboardInterrupt:
+                    _cancel_upload(deployment.id)
+                    raise
 
         toolkit.print_line()
 
diff --git a/tests/test_cli_deploy.py b/tests/test_cli_deploy.py
index 3415eda..64a8c3e 100644
--- a/tests/test_cli_deploy.py
+++ b/tests/test_cli_deploy.py
@@ -990,3 +990,68 @@ def build_logs_handler(request: httpx.Request, route: respx.Route) -> Response:
         result = runner.invoke(app, ["deploy"])
 
         assert "long wait message" in result.output
+
+
+@pytest.mark.respx(base_url=settings.base_api_url)
+def test_calls_upload_cancelled_when_user_interrupts(
+    logged_in_cli: None, tmp_path: Path, respx_mock: respx.MockRouter
+) -> None:
+    app_data = _get_random_app()
+    team_data = _get_random_team()
+    app_id = app_data["id"]
+    team_id = team_data["id"]
+    deployment_data = _get_random_deployment(app_id=app_id)
+
+    config_path = tmp_path / ".fastapicloud" / "cloud.json"
+    config_path.parent.mkdir(parents=True, exist_ok=True)
+    config_path.write_text(f'{{"app_id": "{app_id}", "team_id": "{team_id}"}}')
+
+    respx_mock.get(f"/apps/{app_id}").mock(return_value=Response(200, json=app_data))
+    respx_mock.post(f"/apps/{app_id}/deployments/").mock(
+        return_value=Response(201, json=deployment_data)
+    )
+
+    upload_cancelled_route = respx_mock.post(
+        f"/deployments/{deployment_data['id']}/upload-cancelled"
+    ).mock(return_value=Response(200))
+
+    with changing_dir(tmp_path), patch(
+        "fastapi_cloud_cli.commands.deploy._upload_deployment",
+        side_effect=KeyboardInterrupt(),
+    ):
+        runner.invoke(app, ["deploy"])
+
+        assert upload_cancelled_route.called
+
+
+@pytest.mark.respx(base_url=settings.base_api_url)
+def test_cancel_upload_swallows_exceptions(
+    logged_in_cli: None, tmp_path: Path, respx_mock: respx.MockRouter
+) -> None:
+    app_data = _get_random_app()
+    team_data = _get_random_team()
+    app_id = app_data["id"]
+    team_id = team_data["id"]
+    deployment_data = _get_random_deployment(app_id=app_id)
+
+    config_path = tmp_path / ".fastapicloud" / "cloud.json"
+    config_path.parent.mkdir(parents=True, exist_ok=True)
+    config_path.write_text(f'{{"app_id": "{app_id}", "team_id": "{team_id}"}}')
+
+    respx_mock.get(f"/apps/{app_id}").mock(return_value=Response(200, json=app_data))
+    respx_mock.post(f"/apps/{app_id}/deployments/").mock(
+        return_value=Response(201, json=deployment_data)
+    )
+
+    upload_cancelled_route = respx_mock.post(
+        f"/deployments/{deployment_data['id']}/upload-cancelled"
+    ).mock(return_value=Response(500))
+
+    with changing_dir(tmp_path), patch(
+        "fastapi_cloud_cli.commands.deploy._upload_deployment",
+        side_effect=KeyboardInterrupt(),
+    ):
+        result = runner.invoke(app, ["deploy"])
+
+        assert upload_cancelled_route.called
+        assert "HTTPStatusError" not in result.output