This is an easy target, but MY GOD! On a daily basis I find myself completely irked with Microsoft. As someone who has to create HTML emails
Outlook is a crazy thorn in my side...as it is in everybody else's. I won't even go there because it will boil my blood. Instead I'll focus on something not many people mention, but it's an important point in
UX design. I have 3 hotmail accounts left over from years past. Mainly with email subscriptions and newsletters that I'm too lazy to migrate over. So, the one thing I do enjoy about Hotmail that some other email web-based email apps lack is the ability to switch between accounts without forcing a logout and login. It's handy. Well this isn't:

It's an
incredibly poor design choice. It's your 'sign out' tucked neatly into the drop-down to change user accounts. I'm not an idiot, I'm a pretty damn agile and accomplished mouser, but countless times I've logged out inadvertently. Most annoying thing ever. I don't suspect it will be fixed. It's far too easy.
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