Set-Location -Path WSMan:localhostService;
Set-Item -Path .CertificateThumbprint -Value 'THUMBPRINT';

$yourCred = Get-Credential domainaccount
$yourServer = "your.server.fqdn"

$LatestThumb = Invoke-Command -ComputerName $yourServer `
                            -Credential $yourCred `
                            -ScriptBlock {
                                Get-ChildItem -Path Cert:LocalMachineMy |
                                Sort-Object -Property NotAfter |
                                Select-Object -Last 1 -ExpandProperty Thumbprint
                            }

Set-WSManInstance -ResourceURI winrm/config/Listener `
                  -SelectorSet @{Address="*";Transport="HTTPS"} `
                  -ComputerName $yourServer `
                  -Credential $yourCred `
                  -ValueSet @{CertificateThumbprint=$LatestThumb}

Invoke-Command -ComputerName $yourServer `
               -Credential $yourCred `
               -ScriptBlock { Restart-Service -Force -Name WinRM }