diff --git a/beetsplug/_utils/requests.py b/beetsplug/_utils/requests.py
index b8ac541e9..313ed13b4 100644
--- a/beetsplug/_utils/requests.py
+++ b/beetsplug/_utils/requests.py
@@ -67,7 +67,7 @@ class TimeoutAndRetrySession(requests.Session, metaclass=SingletonMeta):
 
     * default beets User-Agent header
     * default request timeout
-    * automatic retries on transient connection errors
+    * automatic retries on transient connection or server errors
     * raises exceptions for HTTP error status codes
     """
 
@@ -75,7 +75,18 @@ class TimeoutAndRetrySession(requests.Session, metaclass=SingletonMeta):
         super().__init__(*args, **kwargs)
         self.headers["User-Agent"] = f"beets/{__version__} https://beets.io/"
 
-        retry = Retry(connect=2, total=2, backoff_factor=1)
+        retry = Retry(
+            connect=2,
+            total=2,
+            backoff_factor=1,
+            # Retry on server errors
+            status_forcelist=[
+                HTTPStatus.INTERNAL_SERVER_ERROR,
+                HTTPStatus.BAD_GATEWAY,
+                HTTPStatus.SERVICE_UNAVAILABLE,
+                HTTPStatus.GATEWAY_TIMEOUT,
+            ],
+        )
         adapter = HTTPAdapter(max_retries=retry)
         self.mount("https://", adapter)
         self.mount("http://", adapter)
diff --git a/test/plugins/utils/test_request_handler.py b/test/plugins/utils/test_request_handler.py
index c17a9387b..6887283dc 100644
--- a/test/plugins/utils/test_request_handler.py
+++ b/test/plugins/utils/test_request_handler.py
@@ -48,11 +48,20 @@ class TestRequestHandlerRetry:
         assert response.status_code == HTTPStatus.OK
 
     @pytest.mark.parametrize(
-        "last_response", [ConnectionResetError], ids=["conn_error"]
+        "last_response",
+        [
+            ConnectionResetError,
+            HTTPResponse(
+                body=io.BytesIO(b"Server Error"),
+                status=HTTPStatus.INTERNAL_SERVER_ERROR,
+                preload_content=False,
+            ),
+        ],
+        ids=["conn_error", "server_error"],
     )
     def test_retry_exhaustion(self, request_handler):
         """Verify that the handler raises an error after exhausting retries."""
         with pytest.raises(
-            requests.exceptions.ConnectionError, match="Max retries exceeded"
+            requests.exceptions.RequestException, match="Max retries exceeded"
         ):
             request_handler.get("http://example.com/api")