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I have recently performed three Exchange to Office 365 Migrations. In each I have had problems with Office 2016 not connecting to Autodiscover and thus Outlook won't create the profile. In most cases I've used the Microsoft Support and Recovery Assistant to work around this. However, I need to determine what is causing this problem. It's causing a lot of confusion, frustration, and probably hair loss. I've sunk a good 8 hours of troubleshooting, and so far I've had no luck. I'm hoping someone can help. Here's what I've done:

  • I've tested that Autodiscover itself is healthy using TestConnectivity.microsoft.com and by adding profiles on my phone off the network.
  • I have tried to create a profile off the client's network on my own machine.
  • I've tried creating a profile on the network on my own machine, and off the network on the client's machine.
  • You get the picture, basically trying to rule out that a Domain level autodiscover issue is the problem, because that's bit me in the but.
  • I've tried uninstalling Office using the uninstall tool provided my Microsoft and reinstalling Office.
  • I've tried created a new local Windows profile and creating the Outlook profile there.
  • I've tried using registry edits to ignore any and all of the various stages of Autodiscover.
  • I've created a non-AD synced user and tried with that profile to test it's not a problem with the AD attributes coming over the sync.

I'm at a loss at what is causing Outlook to not connect to Office 365. I have three more migrations over the next couple months, so any suggestions y'all have would be appreciated.

Brandon
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  • You haven't said if you've actually disabled the SCP lookup method, either by removing it from AD or disabling that lookup method in Outlook (via GPO). If you haven't then I'd say that's what the problem is. – joeqwerty May 16 '18 at 20:06
  • Sorry, yes, I did specifically try with ExcludeSCPLookup. I went through all those referenced here: https://kb.intermedia.net/article/2445 Also did this on multiple Windows Profiles and on different networks. – Brandon May 16 '18 at 20:15

2 Answers2

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Is it a hybrid environment? In a hybrid environment and during migration, the autodiscover record needs point to On-premise Exchange.

On domain-joined PC, try to configure On-premise Exchange mailbox on Outlook, it will SCP to query AD and find the connection settings. On non-domain-joined PC, try to configure On-premise Exchange mailbox on Outlook. It will use predefined autodiscover process to find the connection settings.

For mailbox in Office 365, autodiscover will do redirect by autodiscover-s.outlook.com and find the connection settings. Refer to: Office 365 Autodiscover Lookup Process

Thus, use ExRCA (switch to Office 365, test it with two mailboxes: one created in Office 365, the one migrated from On-premise) to test Outlook autodiscover.

Jianfei Wang
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Have you tested what lookups the Outlook client makes when it tries to connect?

You can ctrl + rightclick on the Outlook icon down in the task bar. This gives you the option to Test Email Autoconfiguration...

In the test disable Use Guessmart and Secure Guesssmart Authentication. Then enter the Email Address and the Password of the user and hit Test.

In the Log tab you will see all the lookups that autodiscover is trying to do in order to connect to Exchange.

This method will allow you to actually see what the client is attempting and not just secure that the DNS and such is correct.

Look at the log, see if there are any long timeouts and validate if it actually hits the right endpoint in the end or if it gets stuck somewhere.

Henrik Stanley Mortensen
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