Hey Checkyourlogs Fans,
While working through a tenant-to-tenant migration due to a client having an existing tenant hacked. We initiated a project to migrate the existing on-premises environment to a new Office 365 / Azure / EntraID Tenant. We encountered a frustrating issue with the Hybrid Configuration Wizard (HCW). Every attempt to run the wizard would fail at the TestOrgRoute step, resulting in a timeout error and preventing the configuration from being completed. This post outlines the issue, its root cause, and how we resolved it by cleaning up a legacy Hybrid configuration from a now-orphaned tenant.
The Problem
Running the Hybrid Configuration Wizard would consistently fail during the HybridConnectorInstall > TestOrgRoute step with the following error:
The connection to the server ‘1618d77d-df6e-43e0-8a95-513d0f94db07.resource.mailboxmigration.his.msappproxy.net’ could not be completed.
The call to ‘https://1618d77d…/EWS/mrsproxy.svc’ timed out.
Error details:
The request channel timed out attempting to send after 00:00:00.0011023.
Increase the timeout value passed to the call to Request or increase the SendTimeout value on the Binding.
This error was repeated multiple times in the logs with a failure duration of nearly 6 minutes before HCW would throw a hard fail and exit.
Background
In this case, the customer had previously configured Hybrid with a different Microsoft 365 tenant. Due to a recent domain hijack and breach concern, they spun up a new tenant and associated their domain with it. However, their on-premises Exchange 2016 server still had configuration remnants tied to the old tenant.
The HCW was now attempting to reuse this legacy configuration—hence the call to the outdated App Proxy URL, which was no longer accessible or valid. This was the cause of the timeouts.
The Diagnosis
To confirm what was going on, I ran the following from the Exchange Management Shell:
Get-HybridConfiguration
Sure enough, the output showed a previously defined Hybrid setup referencing the old Office 365 tenant. This was utterly incompatible with the new tenant configuration we were trying to establish.
The Fix
To clean up the remnants of the previous Hybrid configuration, we executed the following command:
Remove-HybridConfiguration
This command removes the on-premises configuration settings stored in Exchange and resets the environment, allowing you to run the HCW as if it were being run for the first time.
Important Notes:
- This does not remove any existing connectors or inbound/outbound routes; these may need to be manually reviewed in the Exchange Admin Center (EAC).
- It’s also a good idea to verify the OAuth and IntraOrg connectors are clean if you’re troubleshooting related issues.
Re-running HCW – Success!
After removing the old configuration, we re-launched the Hybrid Configuration Wizard, signed in with credentials for the new tenant, and completed the process without any errors.
Conclusion
If you’re encountering obscure timeout errors with the Hybrid Configuration Wizard—especially during or after a tenant migration—check for any legacy Hybrid configurations that may still be in place.
A quick Get-HybridConfiguration can save you hours of debugging, and running Remove-HybridConfiguration can help reset your environment to get HCW functioning again with the new tenant.
Thanks,
Dave Kawula – MVP
