Can't automatically sign in to the Skype for Business 2016 client at a startup Content provided by Microsoft Applies to: Skype for Business 2016 Select Product Version All Products Symptoms When you start using Microsoft Skype for Business 2016, you find that you can't automatically sign in to the client. This issue occurs even if the single sign-on (SSO) authentication is enabled. Resolution To fix this issue, install the June 4, 2019, update (KB4464576) for Microsoft Skype for Business 2016. Last Updated: Aug 8, 2019 Was this information helpful? Yes No Tell us what we can do to improve the article Submit Thanks! Your feedback will help us improve the support experience.