Helping people with computers... one answer at a time.
My Hotmail "Sent Messages" folder always remains empty, though I sent a number of emails. As a result, I can never confirm they were sent nor review the text again unless I "cc" myself. A search online yielded no results specific to this question nor an email contact for MSN. What's up?
In my humble opinion, Hotmail has several annoyances, and this is another one. I can guess why they do it, but nonetheless it annoys a lot of people.
Hotmail makes saving "Sent Messages" difficult.
Apparently on purpose.
It's very simple, really. When you compose a new message in Hotmail, at the bottom of the message is a checkbox:
Notice how it defaults to being unchecked?
Notice how it defaults to being unchecked for every message you send?
The bottom line is that you must remember to check that box every time you send a message. There's no way that I'm aware of to make "Copy Message to Sent Folder" the default behavior.
If you forget? You're out of luck.
Now, the question is "Why do they do it this way?" My theory, and it's only a theory, is that MSN is worried about server space. If every user saves a copy of every message they send ... that adds up to a lot of messages taking up a lot of space. And more space means more hardware and more cost for MSN. More cost for them for what they provide as a free service.
Certainly there are alternatives. I strongly recommend against any of the free services as your sole email account, or for anything important. (More on why in my article "Are free email services worth it?") But even other free services, such as GMail, do what I consider to be "the right thing" and allow you to save all your sent mail automatically.
So, it's pretty much up to you: remember to check the box each and every time.
Or switch to a different service.