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Outlook 2016 continually prompts for username and password constantly and will not sync

For the past month and a half or so Outlook 2016 will continually prompt for username and password to a point where I have to close it and re open it.  It also will not sync unless I close and reopen it.  This is getting really annoying.  First level support was all but useless.  I'm a network and email tech and have done pretty much everything on my end.  including:

1.  Deleting and recreating my profile, my .ost file, and any other file involved.

2.  Changed my password about 5 times, this will work for about an hour then it starts doing the same thing though it still doesn't sync.

3.  Verified all my settings and tested.

Basically first level support said they don't support 3rd party products like Outlook and to use the webmail.  This is not acceptable.  I read a similar post a couple of weeks ago where moving their account to a different email server solved the trick.  

  • @punster

    It might be easier to try going to webmail and changing your password. Once you've verified the new password is working for webmail, try using it for Outlook and see if that helps.

  • I've changed my password about 20 times.  It will work for about an hour and then pop up with the same *** prompt over and over again.  It's a ** shoot as to whether it will work or not.  

  • @punster

    All of your most recent login attempts look successful. Are you access your mailbox from any sort of hosting provider?

  • I'm going through Cox.  It was doing ok for a short time, now we're back to the same old thing.  Rejected logins.  Finally had to close outlook and re open it.  Sometimes it works, sometimes (most of the time) I get the prompt over and over.

  • Exactly the same way I have to workaround this issue. And it only works for a few times, then back to the same issue. This has been an ongoing issue with Cox for years. Usually, the less experienced techs will advise clearing the browser cache, changing passwords, etc. None of that works.

    Cox techs need to kick this upstairs to more experienced techs to resolve and stop throwing us solutions read from a screen that we've all been through and that don't work.