diff --git a/config/config.default.json b/config/config.default.json
index 0b75b0b..742fdc4 100644
--- a/config/config.default.json
+++ b/config/config.default.json
@@ -6,11 +6,12 @@
   "matrixServerUrl": "http://localhost:8008/",
   "matrixServerName": "localhost",
   // Set this to 100 since that is the max that Synapse will backfill even if you do a
-  // `/messges?limit=1000` and we don't want to miss messages in between.
+  // `/messages?limit=1000` and we don't want to miss messages in between.
   "archiveMessageLimit": 100,
   "requestTimeoutMs": 25000,
   "logOutputFromChildProcesses": false,
   //"stopSearchEngineIndexing": true,
+  "workaroundCloudflare504TimeoutErrors": false,
   // Tracing
   //"jaegerTracesEndpoint": "http://localhost:14268/api/traces",
 
diff --git a/server/middleware/timeout-middleware.js b/server/middleware/timeout-middleware.js
index 3e0428d..0319555 100644
--- a/server/middleware/timeout-middleware.js
+++ b/server/middleware/timeout-middleware.js
@@ -102,8 +102,17 @@ async function timeoutMiddleware(req, res, next) {
       },
     });
 
-    // 504 Gateway timeout
-    res.status(504);
+    // The most semantic HTTP status code to return here is a 504 Gateway timeout but if
+    // you use Cloudflare in front of the archive, it will serve its own
+    // Cloudflare-branded 504 page if your own origin server responds with a 504. And
+    // the only way to disable this functionality is to have an Enterprise Cloudflare
+    // plan. So to workaround this, we return a 500 instead. Relevant Cloudflare docs:
+    // https://developers.cloudflare.com/support/troubleshooting/cloudflare-errors/troubleshooting-cloudflare-5xx-errors/#502504-from-your-origin-web-server
+    //
+    // We want to show our own timeout page because it has more information about what
+    // went wrong (e.g. which external Matrix API requests were slow).
+    res.status(config.workaroundCloudflare504TimeoutErrors ? 500 : 504);
+
     res.set('Content-Type', 'text/html');
 
     res.send(pageHtml);