Sent items show twice on MAIL (IMAP)

Hi everyone!

I need your help! 🙂

As the title suggests, I am experiencing an issue with the Mail app on my MacBook Pro. A few days ago, Hotmail/Outlook announced they started supporting IMAP and I thought that it would be the great way to sync my mail across all my devices (MacBook Pro + iPhone) and proceeded to set up my account as an IMAP account on all of them. Everything went flawlessly... Until today. Indeed, I noticed that when sending e-mails from Mail (OS X), the sent items would show up twice in the sent folder. It is all the more annoying since it syncs across my devices and I get these duplicates on my iPhone and on the web interface as well. Strange thing though, this does not happen when sent from my iPhone (or from the web for that matter), indicating clearly that the issue lies within the Mail app for OS X.

So my question is: does anyone know how to fix this and still let me sync my sent items across all my devices? What are the appropriate settings that I have to use to properly achieve this?

Thank you very much for your help!

Kind regards,

MacBook Pro (13-inch Early 2011), OS X Mountain Lion (10.8.5)

Posted on Oct 4, 2013 3:02 PM

Reply
195 replies

Nov 2, 2015 1:14 AM in response to Valedictorian

Hello!


So after spending hours on the phone with Apple AND Microsoft support, neither were able to figure out the issue. However, I'm proud to say that I think I found the fix. (Worked for me anyways)


On your iOS device (for me it was my iPhone 6s Plus) go to:

-Settings

-Mail, Contacts, Calendars

-Hotmail (under ACCOUNTS) at the very top

-Account

-Advanced

-Sent Mailbox (under MAILBOX BEHAVIORS) at the very top

Now make sure you have the "Sent" at the very top checked under ON MY IPHONE


Now exit out of everything and try sending an email and you should only have one message in your Sent folder instead of the two. Hope this helps!

Jan 14, 2016 11:44 AM in response to sparkle100

I've been dealing with this for awhile on my MacBook (using Apple Mail) with Hotmail (IMAP). And I seem to have found the solution (but I'm surprised no one else has, since it was quite easy...almost to easy).


Here is what I did: On my MacBook I went to Mail >> Preferences >> Accounts >> selected Hotmail >> Mailbox Behaviors >> unchecked "store sent messages on the server" >> and selected "never" for "delete sent messages when:".


Then I ran some tests: I sent an 3 emails, 1 from my Hotmail account in Apple Mail, 1 from my Hotmail account on my iPhone, and 1 from the Web-version of hotmail.....all which resulted in only 1 sent message. Then I checked my sent folders on all devices to see that all 3 emails were represented in sent folders for Apple Mail, my iPhone, and Web-hotmail....which they were.


Problem solved on my end. I'm curious if I've missed something here or if this fixes the issues others are having.

Feb 18, 2016 6:07 PM in response to hargrav8

"store sent messages on the server" is part of the fix for the issue here but the real bug/issue is that MacMail stores the sent item when you click send and then afterwards resyncs with the server, picks up there is another new item in the sent item mailbox (the one we just sent) and downloads it creating the dupe. That is what is happening. I want the sent item left on the server so my other devices can see the sent message and NOT have my sending device clean up after itself by removing it from the server.

_edit: further tests with checking the delete from server option cleans out the whole of my sent items on my mac. Rechecking it will show them all back up.

Jun 3, 2016 12:43 PM in response to hargrav8

The problem seems solved by unchecking the "store sent messages on server," but in my experience, that does not solve the problem. I get the duplicates when REPLYING to emails sent to my hotmail accounts. When I send an email, it does not duplicate. When I reply to an email, I get the duplicates. Called Apple support and the woman told me she's never heard of this problem. LOL. Then she gives me a microsoft number to call and it's an automated answer which hangs up on me after telling me to go search the web.

Jun 25, 2016 9:05 AM in response to Valedictorian

I tried all the solutions presented in this thread and nothing worked. Still getting duplicate sent emails for my outlook.com account in OSX Mail app when replying to email.


Interestingly, I ran multiple tests using the same process, one tested on the Mail app in OSX, other on my Mail app on my iPhone and the last using outlook.com on a browser, and this problem is definitely only happening when replying using the Mail app in OSX. This leads me to believe it's an OSX Mail-specific issue.

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Sent items show twice on MAIL (IMAP)

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