Hybrid Exchange Migration to Exchange Online SSL error

Question

Hybrid Exchange Migration to Exchange Online SSL error

Thomas Dietzius 1

Hello!
I'm struggling with this SSL error message during the On-premises to Microsoft Exchange Online Migration.

Let me give you some information first:

Exchange 2013 - 15.0.1497.2 CU23
AD Sync in place and working
TLS 1.2 is enabled
On firewall SSL inspection is off
Basic Auth activated on the WinRM
MOST IMPORTANT: this have being working for days! We have already migrated a few mailboxes for testing and was working. Now we needed to migrate all the others, it stopped working. No updates or reboots of the Exchange servers have being done.

Do you guys have any ideas?
Thank you!!

Andy David - MVP 157.8K Reputation points

2022-03-16T11:12:07.133+00:00

What do the Hybrid logs say?

https://techcommunity.microsoft.com/t5/exchange-team-blog/modern-hcw-hybrid-agent-troubleshooting-like-a-pro/ba-p/1558725
Thomas Dietzius 1 Reputation point

2022-03-16T12:17:24.107+00:00

Hi AndyDavid,

always the same thing:

ERROR 10085 [Client=UX, Activity=Tenant Connection Validation, Thread=17] Connecting to remote server failed with the following error message: Connecting to remote server outlook.office365.com failed with the following error message : The SSL connection cannot be established. Verify that the service on the remote host is properly configured to listen for HTTPS requests. Consult the logs and documentation for the WS-Management service running on the destination, most commonly IIS or WinRM. If the destination is the WinRM service, run the following command on the destination to analyze and configure the WinRM service: "winrm quickconfig -transport:https". For more information, see the about_Remote_Troubleshooting Help topic.
KyleXu-MSFT 26,396 Reputation points

2022-03-17T06:19:09.477+00:00

Do you try to remove TLS 1.3 and run HCW again?
If could, I would suggest you try to temporarily disable firewall to check whether this phenomenon is related with network filter or proxy configuration on it.

1 answer

Your answer

Andy David - MVP 157.8K Reputation points

2022-03-16T11:12:07.133+00:00

What do the Hybrid logs say?

https://techcommunity.microsoft.com/t5/exchange-team-blog/modern-hcw-hybrid-agent-troubleshooting-like-a-pro/ba-p/1558725
Thomas Dietzius 1 Reputation point

2022-03-16T12:17:24.107+00:00

Hi AndyDavid,

always the same thing:

ERROR 10085 [Client=UX, Activity=Tenant Connection Validation, Thread=17] Connecting to remote server failed with the following error message: Connecting to remote server outlook.office365.com failed with the following error message : The SSL connection cannot be established. Verify that the service on the remote host is properly configured to listen for HTTPS requests. Consult the logs and documentation for the WS-Management service running on the destination, most commonly IIS or WinRM. If the destination is the WinRM service, run the following command on the destination to analyze and configure the WinRM service: "winrm quickconfig -transport:https". For more information, see the about_Remote_Troubleshooting Help topic.
KyleXu-MSFT 26,396 Reputation points

2022-03-17T06:19:09.477+00:00

Do you try to remove TLS 1.3 and run HCW again?
If could, I would suggest you try to temporarily disable firewall to check whether this phenomenon is related with network filter or proxy configuration on it.

Answer 1

Thomas Dietzius 1

So, if that can help someone facing the same issue... I don't have the answer why it didn't work when running the Hybrid Wizard from the Exchange Servers (Windows 2012 R2 updated to the latest update).
But installing the Wizard on another VM with Windows 2019 worked. I don't know what to get from that, but for me it's enough... I can now proceed with the migration and I'll be happy to get rid of those Exchange servers.

Thanks!

Share via

Hybrid Exchange Migration to Exchange Online SSL error

1 answer

Your answer