Microsoft Exchange – Connecting to remote server failed with the following error message

Connecting to Microsoft Exchange via PowerShell is a standard administrative tasks since Exchange 2007 was released.  It's available in all Exchange editions Exchange 2007, Exchange 2010, Exchange 2013, Exchange 2016 and last but not least Microsoft Office 365. To properly manage Exchange you simply need the PowerShell connectivity. While using PowerShell locally doesn't do much checks, during remote connection a lot more things gets checked. One of which are certificates.

While you should always use proper certificates on your servers that's not always the case. If you are sure about the server you're connecting to you can use New-PSSessionOption as part of New-PSSession connectivity.

$sessionOption = New-PSSessionOption -SkipRevocationCheck -SkipCACheck -SkipCNCheck

$EXOSession = New-PSSession -ConfigurationName Microsoft.Exchange -ConnectionUri $URL -Credential $Credentials -Authentication $Authentication -AllowRedirection -Name $sessionName -SessionOption $sessionOption

As you can you see in the example above there are 3 very useful switches for New-PSSessionOption: SkipRevocationCheck, SkipCACheck, SkipCNCheck. Those are in case you get other similar errors when connecting to PowerShell remotely and should solve most of the certificates issues that may arise during connection to powershell. Just make sure the server is trusted. Finally proceed with standard Import-PSSession $EXOSession -AllowClobber.