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The problem: Outlook.com is automatically deleting Sent Mail messages from the Sent folder after three days. I want it to retain Sent messages until I choose to delete them.

Background: This issue started about a year ago. At that time, I had several Outlook.com email addresses (and the aliases associated with each of them) all forwarding into one Outlook.com client (hosted on subdomain bay178). I've been an Outlook.com user since its 2012 rollout, and did not experience this Sent message auto-deletion issue until 2015. I cannot find anything in Outlook.com's Settings options that pertains to Sent message retention.

Now, messages I send are visible in the Sent Mail folder for about 72 hours after sending, and then they simply disappear. They do not go into the Deleted or Archive folders. I keep my Inbox messages organized by conversation, and I am not sure if my replies - which would have originally appeared in the Sent folder, then disappeared after 3 days - are being preserved in these conversation threads or not. (I was able to find some conversations where my replies did appear, but those pre-date this auto-deletion problem.)

Around the same time, but for unrelated reasons, I decided to disable forwarding for one of these email/alias pairs in order to access it via its own separate instance of Outlook.com (hosted on subdomain blu172). This separation of accounts had NO effect on the way Sent messages were being auto-deleted after 3 days on the bay178 subdomain account, but (fortunately!) the blu172 Outlook.com profile does NOT exhibit the Sent messages auto-deletion behavior.

I have researched this issue extensively online but can only find comparable problems reported for Outlook, not Outlook.com. I tried chatting with MS tech support...two frustrating hours later, no joy. They assured me the problem was fixed, but it persists and is very annoying. Any ideas, suggestions, etc. are much appreciated!

  • What's "bay178"? Are you referring to the subdomain you access eg. bay178.mail.Live.com? Or some other service? Is it possible you are accessing your account via an IMAP client and the IMAP client is deleting the emails? – MrWhite Jan 21 '16 at 17:26
  • Yes, that's it. Didn't know it was called the subdomain. When I tried to type the full live.com URL in my question, StackExchange's spam filter wouldn't let me post it. I use Outlook.com's web portal exclusively to access my @outlook.com email account, so no IMAP client would be involved, right? – Laiki Jan 23 '16 at 0:01
  • That doesn't make much sense. I have items in my "Sent" folder from 2014. – ale Jan 23 '16 at 0:18
  • Yes, Al E., that's exactly my opinion: it doesn't make much sense, but it is nonetheless what is happening. – Laiki Jan 24 '16 at 4:33
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The two most likely reasons are:

  • You have an email client attached somewhere that is clearing out (deleting or moving) the emails.
  • You're account is compromised and someone is using it to send emails. They are covering their tracks by clearing out the sent items folder. This one seems unlikely though if you a regularly checking your account & as only 3d old items are being deleted. However, I've seen a lot of this happening over the last 12m on other systems.

I think the first thing to do is to change your password and check any devices that might connect to the account.

  • Thank you, Julian Knight. You have given me a good lead with your reason #1 above, which reminded me that I did download an iOS mail app called Boxer several months ago, and even though I'm not using it, it could be the cause of the Sent mail issue. I will check it out and post back. – Laiki Jan 24 '16 at 4:37
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    For sure, check the recent activity on your account: account.live.com/Activity – ale Jan 24 '16 at 15:46
  • @Julian Knight: Following up on your suggestion, "You have an email client attached somewhere that is clearing out (deleting or moving) the emails" - I deleted my outlook.com profile from the Boxer app, then deleted Boxer on 1/26...but when I checked my Sent folder just now (2/2), there were NO sent messages in it at all, so it appears that approach didn't work. – Laiki Feb 3 '16 at 0:30
  • Correction: I just discovered that Boxer was still installed on another IOS device, and my outlook.com account was still active there (the changes didn't propagate between devices). So now that I've deleted that instance of the account and Boxer, I will give it another three days and post back. – Laiki Feb 3 '16 at 0:38
  • Update Feb 7: Just checked my Sent folder again, and unfortunately the elimination of the Boxer mail app does not seem to have resolved the problem - sent messages dated prior to Feb 5 are gone. – Laiki Feb 8 '16 at 0:07
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I believe I've uncovered the source of the problem by taking a look at my existing Outlook.com rules, where I found this one:

"If in folder Junk and older than 3 days - move to Deleted and mark as read"

I'm wondering if this rule might be the culprit...and maybe I've uncovered a bug in the code where Outlook.com is moving messages that are older than 3 days NOT (or not only) from Junk, as my rule specified, but from Sent, to Deleted.

I trashed the above rule on 20 Feb 2016 (and have NOT recreated it), and today I checked the Sent folder again...all my Sent messages from that date forward are still there.

SUMMARY: As of 2 March 2016, all Sent messages generated from 20 Feb 2016 are still in the Sent folder. That indicates to me there IS a bug in the Rules code (described above). But at least my "Sent Messages disappearing" mystery is solved.

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