Businesses find Skype to be useful, however like any MS product it has quirks. One of them is that even though in the Options it is checked to start the app when logging into Windows, it does not start.
It turns out that to make this work you have to right click on the Skype For Business shortcut on your start menu or desktop. Go to properties. Go to compatibility. Make sure Run as administrator is checked. Restart your computer. Now Skype for business will automatically start.
This is typical for Microsoft. Often MS attempt to make things automatic depend on other things. In this case, Skype probably adapted from its consumer version. It was never made with the kind of security awareness that exist in most business environments. This is probably the logical reason this problem exists.
However this is no excuse for this not working. When something is branded “for business” it sounds as though it were specially designed. Often Microsoft marketing makes its products sound much better than they actually are. Yes, this is the definition of advertising, but it has real world consequences.
This is part of why I am not a fan of Microsoft. For years they promise things will be better, and in some ways they are. However in other ways they are worse, and that affects everyone not just IT people.
It is common to find major problems with MS products. Features get removed and no one is told. Everyday in every job, I learn more things that MS changes and those changes are not make to help their customers but to make things a better business for themselves.
For example, take Office 365. Why is MS so hesitant to offer compatibility with other cloud providers? Do they feel that their OneDrive can’t stand the competition? I believe the answer is yes, otherwise they would support popular third-party file sharing sites.
Gates was famous for saying “embrace and extend and extinguish.” That is, embrace what everyone is doing. Then add proprietary features, and then kill the competition. It has been a long time since MS killed their competition. They just tend to buy them out.