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

Aug 4, 2015 1:34 PM in response to Valedictorian

The best solution I have found to date is to only use the Outlook outgoing server. Using an alternate IMAP server risks having the email flagged as spam as some spam filters (client and server side) consider relaying, and mail sent from a server other than the correct originating email server, spam. I have recently had mail look like it's sent and not received (intercepted by server-side spam filters that recipients don't see. It also risks having the mail server blacklisted).


Untick "store sent messages on server" (in Mac Mail) and do similar on your iPhone (as in, store the Sent emails, "On My iPhone"). Note: I setup my iPhone 6 using IMAP, perhaps Activesync on the iPhone would work better in this regard.


The downside of this is you don't get your SYNCED Sent emails in the "Unified" Sent items folders (the ones with the paper-plane icon) on neither your Mac or iPhone, and you end up with your real sync'd Sent items in a Sent "sub-folder" at the bottom of the IMAP folder list.


The other downside is you can't view ALL sent items across all accounts in Mac Mail using the unified sent folder, but I find these bad for productivity anyway.


The upside of this is you end up with your duplicates in the "paper-plane" Sent folder on each your iPhone and Mac Mail as local copies that were only sent from whichever device. A nuisance perhaps to have to purge it once in a while, but simple enough.....or just ignore them.


Hope this helps.....I'll check this thread once in a while to see if anyone has a better solution using the correct outgoing folder.

Aug 4, 2015 3:11 PM in response to rbkerr

I should add, many people above have said what I have, I just thought it helpful to summarise the best solution as I see it. Using an alternate mail server is a better option (which I did for a long time), but I started getting more than a few people not getting mail, so to avoid being flagged as spam, I've used the option above.

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Sent items show twice on MAIL (IMAP)

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