autodetect was't working when i was connected on-prem... interestingly, it worked fine when i was external so i knew i had a shot... i've seen this issue mentioned in numerous other support forums
typical error message: You're not configured to connect to the server.
steps that worked for me:
- pull working Windows configs by CTRL+RightMouse on Skype tray icon > Configuration Information
- based on educated guess i took the "DG URL Internal/External" https: urls and plugged them into skype's [advanced options] page
- also on windows, i also exported the certificate from the browser for the above server and imported it into mac's keychain
- i exported the .p7b format INCLUDING the parent certificate chain
- i imported as "system" level