Office 365 Migrations – Helpful Tips (5)

In part 5 in my series on helpful troubleshooting tips and resolutions I cover my final troubleshooting tip for moving users to the cloud. This will be the last article on Office 365 for a while so I can concentrate on more on-prem topics which I typically cover in my blog.

When migrating users you can come across a myriad of issues that will prevent a mailbox from moving to the cloud. Anything from Active Directory replication, to invalid email addresses to to many bad items. Some of these are easy to fix, some are not. However, once a user is in Office 365, your problems should be over, right? Not always.

Take for example a user who’s mailbox moved from Exchange 2003 to 2010 to Office 365 without any issues. Not a single hiccup, failed script, etc. Now the user is told their mailbox has moved, go ahead and open up Outlook, enter credentials for the one pop-up and let Outlook reconfigure the profile in conjunction with Autodiscover for a seamless experience. This same user, however, receives another login prompt and again the end user puts in credentials and checks the ‘remember’ check box. Yet they continue to receive authentication pop-ups. How do we resolve/troubleshoot this?

  • Verify the credentials are correct. Does the UPN they are using ( match what is listed on their user account.
  • Verify the users computer has the Single Sign On Assistant installed.
  • Verify the PC has all the latest updates for Office.
  • Verify other updates using Office 365 Desktop Software tool.
  • Verify Office 365 license for the user

For this situation, I verified all of these items. Still getting a prompt. I then logged in as my admin user account, created a profile for the user and connected without issue. The user then logged in as themselves and we tried Outlook Web Access which worked as well. It dawned on that maybe IE had a proxy connection as this controls some of Outlook’s connectivity to Exchange/Office 365. In IE go to Tools –> Internet Options –> Connections –> LAN Connections –> “Use a Proxy Server…” was selected and a proxy server was listed. I removed the proxy server. Then reopened Outlook and Outlook connected and he was able to download his mailbox from Office 365.

I’ve now added this to my list of items to check when there are connection issues. Hope this helps others when troubleshooting the issues.

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