diff --git a/extensions/browser/api/web_request/web_request_api.cc b/extensions/browser/api/web_request/web_request_api.cc
index 6d4af39e1575043ebc433aeb38a7fdac4247d608..79d9ddf91a411edc0e7f6a17b5eaf1cdc5c55424 100644
--- a/extensions/browser/api/web_request/web_request_api.cc
+++ b/extensions/browser/api/web_request/web_request_api.cc
@@ -1385,6 +1385,9 @@ 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 ||