diff --git a/nextcloud_mcp_server/auth/oauth_routes.py b/nextcloud_mcp_server/auth/oauth_routes.py
index 1a726a29..1eb39286 100644
--- a/nextcloud_mcp_server/auth/oauth_routes.py
+++ b/nextcloud_mcp_server/auth/oauth_routes.py
@@ -136,13 +136,18 @@ def _transform_scopes_for_idp(scopes: str, resource_server_id: str) -> str:
 
 
 async def _get_cached_discovery(url: str) -> dict[str, Any]:
-    """Fetch OIDC discovery document with caching (5-minute TTL)."""
+    """Fetch OIDC discovery document with caching (5-minute TTL).
+
+    Follows redirects so the configured discovery URL works against Nextcloud
+    instances without pretty URLs enabled, where ``/.well-known/openid-configuration``
+    issues a 301 to ``/index.php/.well-known/openid-configuration``.
+    """
     now = time.time()
     if url in _discovery_cache:
         expires_at, data = _discovery_cache[url]
         if now < expires_at:
             return data
-    async with nextcloud_httpx_client() as http_client:
+    async with nextcloud_httpx_client(follow_redirects=True) as http_client:
         response = await http_client.get(url)
         response.raise_for_status()
         data = response.json()
diff --git a/tests/unit/test_oidc_discovery.py b/tests/unit/test_oidc_discovery.py
new file mode 100644
index 00000000..c2459f25
--- /dev/null
+++ b/tests/unit/test_oidc_discovery.py
@@ -0,0 +1,61 @@
+"""Unit tests for OIDC discovery fetch in oauth_routes."""
+
+from unittest.mock import patch
+
+import httpx
+import pytest
+
+from nextcloud_mcp_server.auth import oauth_routes
+from nextcloud_mcp_server.auth.oauth_routes import _get_cached_discovery
+
+pytestmark = pytest.mark.unit
+
+
+@pytest.fixture(autouse=True)
+def _clear_discovery_cache():
+    """Reset the in-memory discovery cache between tests."""
+    oauth_routes._discovery_cache.clear()
+    yield
+    oauth_routes._discovery_cache.clear()
+
+
+async def test_discovery_follows_redirect_to_index_php():
+    """Discovery fetch must follow 301s.
+
+    Hetzner StorageShare and other Nextcloud installs without pretty URLs
+    redirect ``/.well-known/openid-configuration`` to
+    ``/index.php/.well-known/openid-configuration``. Without follow_redirects
+    the OAuth authorize handler raises HTTPStatusError and returns 500
+    (see oauth_routes._get_cached_discovery).
+    """
+
+    pretty_url = "https://nx.example.com/.well-known/openid-configuration"
+    rewritten_url = "https://nx.example.com/index.php/.well-known/openid-configuration"
+    discovery_doc = {
+        "issuer": "https://nx.example.com",
+        "authorization_endpoint": "https://nx.example.com/index.php/apps/oidc/authorize",
+        "token_endpoint": "https://nx.example.com/index.php/apps/oidc/token",
+    }
+
+    def handler(request: httpx.Request) -> httpx.Response:
+        if str(request.url) == pretty_url:
+            return httpx.Response(301, headers={"location": rewritten_url})
+        if str(request.url) == rewritten_url:
+            return httpx.Response(200, json=discovery_doc)
+        return httpx.Response(404)
+
+    transport = httpx.MockTransport(handler)
+
+    def fake_client(**kwargs):
+        kwargs["transport"] = transport
+        return httpx.AsyncClient(**kwargs)
+
+    with patch(
+        "nextcloud_mcp_server.auth.oauth_routes.nextcloud_httpx_client",
+        side_effect=fake_client,
+    ) as factory:
+        result = await _get_cached_discovery(pretty_url)
+
+    assert result == discovery_doc
+    factory.assert_called_once()
+    assert factory.call_args.kwargs.get("follow_redirects") is True