Hello all.
I had this problem recently. Skype for Business 16 is stuck at "Contacting server and signing in..." and doesn't give any error.
I tried the solutions stated here:
https://answers.microsoft.com/en-us/msoffice/forum/msoffice_sfb-mso_win10/what-causes-skype-for-business-not-to-sing-in-and/fc05d5ac-e5cc-4289-ae7f-50b94fd39a92
It didn't work, I also tried other solutions on the internet.
I don't have any problems with the account, because I can sign in from another computer.
It has been several days now, and I couldn't sign-in once from my own computer.
Attention: I might be in the wrong track regarding to following explanations, I just think it may be the cause but not sure.
It may be a certificate error, I checked the connections in netstat when Skype was trying to connect.
There were different connections which were direcly going to IP addresses and putting them on my browser first gave me the certificate is not trusted error and then continuing to address took me to the office365 sign-in page. Example:
netstat show a connection established to there but browser gives certificate error: https://132.245.61.226/
The address it takes me and doesn't give me a certificate error here(removed some parts from link): https://login.microsoftonline.com/login.srf?wa=wsignin1.0&[removed]&wreply=https%3a%2f%2f132.245.61.226%2fowa%2f&[removed]
I would be really glad if someone could help. I am logging in from an RDP environment right now but need to solve it on my PC.