Configuring preferences and options in Outlook.com
I also almost just missed an appointment because of this bug. Went to search for this right away because it's really, really annoying! Can actually dent my reputation (diminished reliability - which is practically a currency in what I do) and ultimately even cost me (and others) money.
Am using the desktop version of Outlook for the first time in more than a year and will be using it on a daily basis for at least a few months; I will have to deal with this on a daily basis. I agree with most comments here that this is no feature but a bug. It never used to work like this and still doesn't in the online version of Outlook and it just simply makes no sense whatsoever to show where in your agenda you were yesterday at this (current) time (and not showing where in your agenda you are right now). Really hope MS solves this very soon!