Make sure you enable TLS1.2 first:
[Net.ServicePointManager]::SecurityProtocol = [Net.SecurityProtocolType]::Tls12
Other than that, make sure you have the latest updates, at minimum the Trusted root CA ones.
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Hi,
I’m getting the below error when I try to connect exchange online using PowerShell from my Server 2012 R2
New-ExoPSSession : 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.
At C:\Program
Files\WindowsPowerShell\Modules\ExchangeOnlineManagement\2.0.5\netFramework\ExchangeOnlineManagement.psm1:475 char:30
Make sure you enable TLS1.2 first:
[Net.ServicePointManager]::SecurityProtocol = [Net.SecurityProtocolType]::Tls12
Other than that, make sure you have the latest updates, at minimum the Trusted root CA ones.
Whether there exists firewall in your organization, if so, I would suggest you try to disable it temporarily to check whether this phenomenon is caused by it. You need to make sure Office 365 URLs and IP address ranges could access from your client successfully.
I also suggest you have a check whether there exists proxy setting on your client. If there is, try to remove it and connect to Exchange online again.
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