Christ on a bike, the state of Outlook on Windows is absolutely miserable. I knew it by experience when I started preparing HTML signatures for our company, but seeing the list makes me even sadder about the absolute state of incompetency caused by legacy systems in Microsoft. For those uninformed, Outlook on Windows effectively works on a terrible (and terribly old) implementation of HTML that was initially developed for Word from 2001 (or older, can't remember exactly).
The Outlook ecosystem has to die.