Fix: Hybrid Configuration Wizard unable to connect to Office 365

If you’ve got a Microsoft 365 tenant created after late March 2023 (or you’re otherwise reading this in June 2023), you may find that you are faced with the below error when running the Hybrid Configuration Wizard (HCW):

Connecting to remote server failed with the following error message: Connecting to remote server outlook.office365.com failed with the following error message: The server certificate on the destination computer (outlook.office365.com:443) has the following errors: Encountered an internal error in the SSL library. For more information, see the about_Remote_Troubleshooting Help topic.

This is because Microsoft has began disabling Remote PowerShell in Exchange Online, starting with new tenants. In early April they promised an update would arrive “soon” which would fix HCW, however May is quickly approaching with the issue still outstanding.

To fix this, you simply need to (re)enable RPS support, using either Microsoft’s self-service tool or alternaively using the “Help & Support” page within your Microsoft 365 admin centre. Details on both methods can be found here.

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