diff --git a/server/api_server/mcp_endpoint.py b/server/api_server/mcp_endpoint.py
index 424484fbd..64280d8aa 100644
--- a/server/api_server/mcp_endpoint.py
+++ b/server/api_server/mcp_endpoint.py
@@ -1057,8 +1057,9 @@ def mcp_sse():
 
     def stream():
         """Generator for SSE stream."""
-        # Send endpoint event with session ID
-        yield f"event: endpoint\ndata: /mcp/messages?session_id={session_id}\n\n"
+        # Send endpoint event with session ID. Relative path, so clients resolve it against
+        # the SSE URL they used (works directly and behind the nginx /server prefix).
+        yield f"event: endpoint\ndata: messages?session_id={session_id}\n\n"
 
         try:
             while True:
diff --git a/test/api_endpoints/test_mcp_sse_endpoint.py b/test/api_endpoints/test_mcp_sse_endpoint.py
new file mode 100644
index 000000000..44555b511
--- /dev/null
+++ b/test/api_endpoints/test_mcp_sse_endpoint.py
@@ -0,0 +1,46 @@
+from urllib.parse import urljoin, urlparse
+
+import pytest
+
+from api_server.api_server_start import app
+from helper import get_setting_value
+
+
+@pytest.fixture(scope="session")
+def api_token():
+    """Return the API token from the loaded config."""
+    return get_setting_value("API_TOKEN")
+
+
+@pytest.fixture
+def client():
+    """Yield a Flask test client for the API server."""
+    with app.test_client() as client:
+        yield client
+
+
+def read_endpoint_event(client, api_token):
+    """Open the MCP SSE stream and return the data of its first (endpoint) event."""
+    response = client.get("/mcp/sse", headers={"Authorization": f"Bearer {api_token}"}, buffered=False)
+    assert response.status_code == 200
+    try:
+        first_event = next(response.response)
+    finally:
+        response.close()
+    if isinstance(first_event, bytes):
+        first_event = first_event.decode()
+    lines = first_event.strip().splitlines()
+    assert lines[0] == "event: endpoint"
+    return lines[1].removeprefix("data: ")
+
+
+@pytest.mark.parametrize("sse_url, expected_path", [
+    ("http://host:20212/mcp/sse", "/mcp/messages"),
+    ("http://host:20211/server/mcp/sse", "/server/mcp/messages"),
+])
+def test_sse_endpoint_resolves_to_messages_route(client, api_token, sse_url, expected_path):
+    """The advertised endpoint must resolve to the messages route both directly and behind the /server proxy prefix."""
+    endpoint = read_endpoint_event(client, api_token)
+    resolved = urlparse(urljoin(sse_url, endpoint))
+    assert resolved.path == expected_path
+    assert resolved.query.startswith("session_id=")