You may come across while configuring the Synch Service to connect to Azure via a Proxy, upon clicking 'Test Connection' the following error may be displayed:
"Connecting to remote server ps.outlook.com failed with the following error message: The client cannot connect to the destination specified in the request.
Verify that the service on the destination is running and is accepting 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". For more information, see the about_Remote_Troubleshooting Help topic.." “
1) Please make sure the O365 account used been enabled for Remote Powershell (note: you may need to load the Exchange Powershell module and connect to tenet beforehand):
2) Check if a Proxy Server been configured for WinRM:
netsh winhttp show proxy
3) If result of step 2) is a expired proxy server, please try to reset its settings and configure a new proxy server for WinRM using this commands below:
netsh winhttp reset proxy
netsh winhttp set proxy