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[Solved] Error 500 – SSL Connection cannot be established

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Topic starter

We’re getting the following message when trying to connect to our mailbox-server.
The strange thing is that it sometimes work.
This morning I was able to create a new mailbox without issues but when I went back a couple of minutes later to do some changes I ended up with the error.

Connecting to remote server xxxxxxxx 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.

4 Answers
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Please make sure that basic authentication is enabled on the powershell virtual directory for that specific server. Check this with EAC and don’t use IIS to set that value.

SupportUppsala Topic starter 2016-04-07 20:08

Basic authentication is enabled on the virtual directory. I’ve even disabled it and re-enabled it.

We’re connecting directly to one of the mailbox servers and we’re not using a load balancer.

Jacob Dixon 2016-04-08 02:31

That is very odd… I haven’t seen this where it happens randomly unless there is some sort of communication issue (like the server dropping off the network). Have you tested pointing it to another server?

Also you mentioned you were pointing it to a mailbox server… is your environment 2013 and your client access and mailbox server is combined?

SupportUppsala Topic starter 2016-04-08 02:45

The server is 2016 – multirole.
I tried pointing to our second mbx-server and it seems to work. That’s strange since the configuration on the servers are identical.

I just noticed another issue – don’t know if it has anything to do with this:
When trying to create a new user/mailbox I get the following error:

Couldn’t find recipient “de557de6-b606-44f9-bf86-e62f94a33471”.

Jacob Dixon 2016-04-08 04:00

Where are you seeing that error? That is very off. Ca nyou tell me what verison you are running?

Jacob Dixon 2016-05-02 14:45

Johan, Are you still having this issue? If so then it may be time to do a remote session.

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Also are you pointing to a load balancer at all?

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I do also have this problem ?

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Thanks!

That led me in right direction. I’m using Let’s Encrypt certificate on my Exchange server. The renewal of the certificate did not change to new certificate on all bindings. So on the Exchange server the *:443 and 127.0.0.1:443 did not have a certificate assigned. After assigning one, it works again.
I found out because https://localhost/ecp did not work and it worked from the outside.

Thanks for your help 🙂

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