Given Microsoft's recent support reputation, I almost hate to suggest it; but have you tried looking through their FAQs for Outlook.com?

Regardless of how bad, or how good, a program is, you have to get to know it in order to drive on the right side of the bomb craters. You likely won't find answers to the questions that seem most important to you now; but the things you do find may help you get sufficiently more acquainted with how it works to make it easier to work around the nits until you do find your answers.

If you wanna know how it works, ya gotta waste some time with it.

John