diff --git a/isic_cli/cli/user.py b/isic_cli/cli/user.py
index 3a9cd23..98b013e 100644
--- a/isic_cli/cli/user.py
+++ b/isic_cli/cli/user.py
@@ -1,8 +1,10 @@
 from __future__ import annotations
 
 import json
+import sys
 from typing import TYPE_CHECKING
 
+from authlib.integrations.base_client.errors import OAuthError
 import click
 
 if TYPE_CHECKING:
@@ -22,8 +24,18 @@ def login(obj: IsicContext):
     if obj.user:
         click.echo(f'Hello {obj.user["email"]}!')
     else:
-        obj.oauth.login()
-        click.echo("Success!")
+        try:
+            obj.oauth.login()
+        except OAuthError as e:
+            if e.error == "invalid_grant":
+                click.secho(
+                    "Logging in timed out or had an unexpected error. Please try again.", fg="red"
+                )
+                sys.exit(1)
+            else:
+                raise
+        else:
+            click.secho("Success!", fg="green")
 
 
 @user.command()
diff --git a/tests/test_user.py b/tests/test_user.py
index bd5d84f..d8e692d 100644
--- a/tests/test_user.py
+++ b/tests/test_user.py
@@ -1,5 +1,7 @@
 from __future__ import annotations
 
+from authlib.integrations.base_client.errors import OAuthError
+from girder_cli_oauth_client import GirderCliOAuthClient
 import pytest
 
 
@@ -8,3 +10,15 @@ def test_user_login_logged_in(cli_run):
     result = cli_run(["user", "login"])
     assert result.exit_code == 0
     assert "Hello" in result.output
+
+
+@pytest.mark.usefixtures("_isolated_filesystem")
+def test_user_login_oauth_timeout(cli_run, mocker):
+    mock_login = mocker.patch.object(
+        GirderCliOAuthClient, "login", side_effect=OAuthError(error="invalid_grant")
+    )
+
+    result = cli_run(["user", "login"])
+    assert result.exit_code == 1
+    assert "Logging in timed out or had an unexpected error" in result.output
+    mock_login.assert_called_once()