We have our domain setup in Office 365. All email is in Office 365; no local exchange servers. We use AD Connect with Pass-Thru Authentication. Workstations have Office 365 Pro (2016).
We want users to auto-login to Skype at login.
We have Skype loading on login.
We have set the SIP address for the local domain user accounts to their UPN.
We enabled AD Connects Single Sign On.
We created a new test user. When logging in for the 1st time, Skype loads, it's username field is correctly populated with the test users UPN, but the password field is blank, Save Password is checked and it's waiting for the Sign-On button to be clicked. If we load Outlook, it configures itself perfectly. Only need to click a few buttons.
Is Skype special?