"The server certificate on the destination computer has the following errors: Encountered an internal error in the SSL library" while trying to enter a PowerShell session using SSL

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Posted on by Nitin Gaur

Hi Experts,

We are having an issue trying to establish a PowerShell session between two machines. so Machine A is on prem and Machine B is in our Azure tenant. Machine A tries to open a powershell remote session on machine B and gets following error

Connecting to remote server failed with the following error message : "The server certificate on the destination computer has the following errors:
Encountered an internal error in the SSL library"

To test we used a simple command Enter-PSSession -Computername XXXX -UseSSL

This happens only when we use SSL and session is open if we do not provide a -UseSSL with Enter-PSSession command.

The connectivity is available and the service account used is an admin on the target machine (we can open a RDP session) so no issues there.