Parallels running Shared Network, can't get Windows 10 Outlook and Skype to authenticate

Contributor III

Hi all,

I am trying to get Outlook and Skype for Business within Windows 10 working properly.
Our setup is Macbook > Parallels 14.1 > Windows 10. Parallels (Win10) is connecting to Mac via Shared Network (recommended). We need to use shared network because the Macbook is using VPN. Bridge network mode would not work at all.

Anyway, when connected as above, the Windows 10 session cannot start Outlook or SfB properly. it is always asking for user credentials. The rest of the network seems to be working because from a browser (within Windows session), I can access websites that are only available within VPN (company's network).
So what is required to be setup within Parallels' configuration to make the network work for Outlook and Skype for Business?