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.
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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.
Annoying.
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.
Related:
Ask Leo! - Are free email services worth it?
Ask Leo! - All articles on MSN Hotmail
Article C2600 - March 22, 2006
I'm with Saac. Can you retrieve hotmail sent messages from a year ago? hack into your account somehow? I now realise my stupidity in using this account but thought they saved them automatically. Would be very valuable to me at the moment....
Posted by: karina at November 9, 2007 4:07 AMI have an msn account I access through hotmail and msn (the butterfly). All mail I receive I see in both hotmail and msn. I do not see any properly captured 'sent' messages via hotmail in my MSN. Has anyone ever experienced that or know why that is. I use the MSN account only for backing-up my mail in hotmail and I cannot backup my sent messages because MSN doesn't see them???
Posted by: Frank Kotulak at December 16, 2007 3:50 PMi'm sure msn is not short of money.. Even so, if they're were worried about server space, they could warn that "All sent messages with more than 'x' days old will be deleted"...easy, isn't it?
Posted by: Edd at January 5, 2008 7:46 AMHow do I save sent messages automatically everytime?
Posted by: Lisa W. Summerlin at January 17, 2008 1:11 PMIf all users start reminding Hot Mail (MSN) administrators that we need the feature that automataically saves the sent messages, perhaps they would listen. Perhaps someone should write to Bill Gates directly (if they have his address).
Posted by: Robert of New York at August 7, 2008 8:18 PMWe should all demand what we need.
Great. Thanks for the help regarding MSN sent messages! Yes it is a pain and I hope it will one day be changed!
Posted by: Jo Branham at August 20, 2008 10:00 AMI still don't have a direct answer to the following question I asked, Leo! Please respond.
Posted by: Lilly at October 9, 2008 6:48 AM"Where did the option to save sent messages in both msn's and my computer's sent folders go? It used to be there until recently. Now, it only saves on my computer folder. Does this option not exist anymore?"
I have two hotmail accounts and one has this problem with not saving to my sent folder automatically. But my other account does this automatically. Every emnail I sent gets forwarded to my sent folder and I can go into this sent folder to confirm that an email was sent and on what day. But I do clean up this folder every now and then. (every 6 weeks) So my question is why is one account different that another?
Posted by: Slides5 at March 4, 2009 11:19 AMOne day I could go to my sent messages and the next day it was gone. Makes me want to quit msn.
Posted by: Gaye Kloster at March 9, 2009 3:02 PMI'm am very irratated that my MSN account (that I was forced to use with teh purchase of my computer) now forces me to the msn.com/hotmail.com and will not show me my sent messages...yahoo to msn...losers
22-Aug-2009
Posted by: Rebecca at August 21, 2009 6:00 PM