Azure AD Connect/Sync no longer working after in place Server 2016 to 2022 upgrade

Question

I recently performed an in place upgrade from Server 2016 to Server 2022, and after the upgrade was completed, Azure AD Sync no longer seems to function. I am running the most recent version of Azure AD Connect (2.2.1.0) and I have already attempted uninstalling and reinstalling Azure AD Connect with no success. The installation goes fine and by everything I can see on the local server the sync is performed and is successful, however in the Azure Health Portal there are no completed syncs since the upgrade. There are also no sync errors shown other than the sync has not been completed in over 24 hours.

Any help is greatly appreciated.

Answer 1

Hi @Anthony Rico , It's recommended not to perform an in-place upgrade of the OS for your Azure AD Connect server. Instead, you should prepare a new server with the desired operating system and perform a swing migration. Since you have already performed an in-place upgrade, you can try the following steps:

1. Check if you have made any changes to the out-of-box synchronization rules. If so, these rules might be set back to the default configuration on upgrade.
2. If you are using non-standard connectors, refresh the corresponding connector configuration in the Synchronization Service Manager after the in-place upgrade.

If the issue persists, you may need to consider setting up a new server with the desired operating system and perform a swing migration as recommended in the documentation.

We can also open a free support ticket for you to save you some pain. Please let me know and I can help you further.

If this answer helps you please mark "Accept Answer" so other users can reference it.

Thank you,

James

Answer 2

I would note that in place upgrades of the Windows O/S are supported with AADConnect:

https://learn.microsoft.com/en-us/azure/active-directory/hybrid/connect/how-to-upgrade-previous-version