diff --git a/server/server/lib/object-storage/proxy.ts b/server/server/lib/object-storage/proxy.ts
index bef899fed..af37029f8 100644
--- a/server/server/lib/object-storage/proxy.ts
+++ b/server/server/lib/object-storage/proxy.ts
@@ -83,6 +83,8 @@ function handleObjectStorageFailure (res: express.Response, err: Error) {
     return res.sendStatus(HttpStatusCode.NOT_FOUND_404)
   }
 
+  logger.error('Object storage failure', { err })
+
   return res.fail({
     status: HttpStatusCode.INTERNAL_SERVER_ERROR_500,
     message: err.message,
diff --git a/server/server/middlewares/error.ts b/server/server/middlewares/error.ts
index 706009795..51012af07 100644
--- a/server/server/middlewares/error.ts
+++ b/server/server/middlewares/error.ts
@@ -17,11 +17,6 @@ function apiFailMiddleware (req: express.Request, res: express.Response, next: e
       error: message
     })
 
-    res.status(status)
-
-    if (!res.headersSent) {
-      res.setHeader('Content-Type', 'application/problem+json')
-    }
 
     const json = new ProblemDocument({
       status,
@@ -37,6 +32,12 @@ function apiFailMiddleware (req: express.Request, res: express.Response, next: e
 
     logger.debug('Bad HTTP request.', { json, tags })
 
+    res.status(status)
+
+    // Cannot display a proper error to the client since headers are already sent
+    if (res.headersSent) return
+
+    res.setHeader('Content-Type', 'application/problem+json')
     res.json(json)
   }