If the error occurs unfrequently and randomly, it's probably coming from the server for example due to a time out after a long period of server inactivity.
As noticed by tek_siri, the best would be either to use fiddler to observe the requests or to log the events at server side. But if you can't reproduce the issue, it's hard to debug.
If most generally the second user attempt after a fail is working, you might implement it by code, i.e. in the Failed Handler, retry once to execute the request.