diff --git a/extensions/browser/api/web_request/web_request_api.cc b/extensions/browser/api/web_request/web_request_api.cc
index f3bdc2025a0febce845b09bcf8b8b811d10a4b05..578620d841c0a4aa96a5d044d03c30c4a9673db2 100644
--- a/extensions/browser/api/web_request/web_request_api.cc
+++ b/extensions/browser/api/web_request/web_request_api.cc
@@ -1388,6 +1388,9 @@ ExtensionWebRequestEventRouter::OnAuthRequired(
     const net::AuthChallengeInfo& auth_info,
     AuthCallback callback,
     net::AuthCredentials* credentials) {
+  ClearSignaled(request->id, kOnBeforeSendHeaders);
+  ClearSignaled(request->id, kOnSendHeaders);
+  ClearSignaled(request->id, kOnHeadersReceived);
   // No browser_context means that this is for authentication challenges in the
   // system context. Skip in that case. Also skip sensitive requests.
   if (!browser_context ||