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The problem occurs in different versions of Outlook (2019/2016/365) and Windows (there was a problem in both Windows 7/8.1 and Windows 10).

okay, thank you. so this should stop the constant password popup window once it propagates? Okay.

Even though I got this working for me, could it possibly happen to someone else? When you open Outlook hold crtl+right click the Outlook icon and select Test Email AutoConfig. Not without someone doing it. I will just award you all the points on one of the fixes. No, we are all on Exchange 2007 or 2010.  thanks again for all your help, since you helped me all the way through. Having these 2 URL improperly configured can cause password prompting issues. Clear your cached password - Mac.

I set up a testclient and have the same issue.

You have to ctrl/right click on the Outlook icon in the system tray, not the icon on the toolbar. Exchange Web Services synchronization, notification, availability, and Automatic Replies. That fixed the problem. He has this issue when hes connecteced locally or remote via VPN or Outlook Anywhere. (Get your first solution completely free - no credit card required).

Even I get this on my phone, the password pop up window.

Run the Autodiscover test and view all of your URL's for Exchange. Our community of experts have been thoroughly vetted for their expertise and industry experience. In Outlook 2007, this problem is caused by a known bug but there is no known bug that can cause this problem in another version of MS Outlook. but after some couple of days, outlook again stop sync and ask for password. Find answers to Exchange 2010 Outlook keeps asking for password from the expert community at Experts Exchange Privacy Policy and But it could have occurred as a result of internal or external DNS changes. The results of the test was - Autoconfiguration was unable to determine your settings.

Where do I go from here?

It can definitely contribute to that problem.

You will need to go into your external DNS. It appears to have something to do with auto discover. How do I reconfigure it to point to my external IP? By clicking the “Cancel” button, the user can continue to work with Outlook, but after a while the window asking for the password pops up again (sometimes the user account may be locked at the same time).

Yesterday I got it once and figured it would stop, but got it again first thing this morning.

I think I will investigate disabling Mapi over http for now till we upgrade our clients from outlook 2010 to 2016 in the near future.

yes, it is on the certificate.

*This site is protected by reCAPTCHA and the Google https://www.experts-exchange.com/questions/28611965/Exchange-2010-Outlook-keeps-asking-for-password.html, https://www.experts-exchange.com/Software/Office_Productivity/Groupware/Outlook/Q_28599602.html, https://cvhsinc.org:443/Autodiscover/Autodiscover.xml, https://autodiscover.cvhsinc.org:443/Autodiscover/Autodiscover.xml, https://autodiscover.cvhsinc.org/autodiscover/autodiscover.xml, https://exchange2010.cvhs.lan/ews/exchange.asmx, https://exchange2010.cvhsinc.org/ews/exchange.asmx, https://exchange2010.cvhsinc.org/exchange.asmx, http://certs.starfieldtech.com/repository/, https://cvhisnc.org:443/Autodiscover/Autodiscover.xml, https://autodiscover.cvhisnc.org:443/Autodiscover/Autodiscover.xml. We are seriously considering Office 365.

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