Select all credentials for Microsoft, Outlook, OneDrive, or Skype for Business and choose Remove from Vault. Choose Start | Control Panel | View by Large Icons (upper right of window) | User Accounts | Manage your credentials (left column). Clear your cached passwords (Note: you may need Admin rights to do this) - Windows. Mac Outlook - Choose Tools | Accounts | type your HawkID password in the password field. Deselect the "Always prompt for logon credentials" check box. If prompted, in the Password: text box, type your password. Choose File | Account Settings | Account Settings. Verify that prompt for Credentials isn’t checked in profile:. If prompted again after Cancel, move on to step 3. Be sure to use when prompted for your Outlook credentials and check the " remember credentials" box. Try logging into Outlook on the web? If you can log into Outlook on the web, then try restarting Outlook. It will run diagnostics and attempt to fix the issue. If the steps below don't work, download and install the Microsoft Support and Recovery Tool. In this case, please contact your local ITS Support Team or the ITS Help Desk. In some cases, you may need administrative rights to update these settings. Thoughts\issues: Will Exch 2010 behave correctly while demoting "server2" and then adding the machine to the domain? Is it possible to go directly to Exch 2019 from Exch 2010 or do I have to create an Exch 2016 as an interim step? I would really hate to export all the mailboxes, remove Exch 2010, bump the forest, install Exch 2019, and import the mailboxes.If you are continually being prompted for your password in Outlook try the steps below, one at a time, to resolve the issue. Then possibly bump the forest level to current? Then move the mailboxes from the 2010 store to the 2019 store. 
Then bump the forest level to 2012? Then install Exch 2019 to its own guest. Exchange likely will complain about no DC but then add as member of the 2019 guest DC. So, after I move the file share and SQL to their own guests (everything on single physical machine currently) plan is to demote current "server2". Have a 2019 guest as a DC but forest level still 2008 R2. Exch 2019 requires level to be 2012+.
Here are my problems\thoughts?Ĭurrent environment is: Single 2008R2 server, AD, Exch 2010. Old installation getting around to upgrading.
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