Outlook 2010, 2013 on new 2010 exchange server get windows security popup for password

We recently migrated exchange 2003 on 2003 server to Server 2008R2 and Exchange 2010 SP3. The installation had multiple problems and we resorted to Microsoft technical support for the server resolution. On the server level it seems to function
as expected. Our problem is with outlook 2010 and 2013. Some of these outlook 2010 installs existed prior to the exchange 2010 upgrade and worked as expected prior to the upgrade
Now with new machines (never been connected to our Domain) and some existing windows 7 machines with outlook 2010 and 2013, we get a windows security popup requesting the password.
We have spent a couple of weeks reading blogs, how two's and guaranteed fixes that don't fix. The best we can do is start outlook, get the folders to sync and shortly thereafter it will request the password. You can enter the password and
it comes right back requesting the password. You can cancel the request and you will get needs password in the area where it shows connected to exchange server and then will not prompt for another password until you need an update from the server
or you try to send and email. The email will not send until provide a password and immediately press send. Once in the outbox it will require the password again to send and then cancel the popup and repeat the process again.
Outlook test, turn off discovery, remove all credentials do not help. Outlook anywhere turned off. So far nothing seems to help.
Does anybody have a solution to my dilemma?

Hi,
Please check the problematic users' Outlook settings by the following steps:
1. Click File > Account Settings > Account Settings > Change > More settings.
2. In Security tab, make sure "Encrypt data between Microsoft Outlook and Microsoft Exchange" option is checked, "Always prompt for logon credentials" is unchecked.
3. Change the logon network security to Negotiate Authentication, and Apply > OK to set it.
Restart Outlook to have a try. If the issue persists, please
re-create Outlook profile to check whether the issue persists.
Regards,
Winnie Liang
TechNet Community Support
Thank you for the response.
I did as you suggested and the problem persists

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