Valedictorian

Q: 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

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Q: Sent items show twice on MAIL (IMAP)

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  • by Valedictorian,Helpful

    Valedictorian Valedictorian Nov 18, 2013 5:19 AM in response to Octaviofb
    Level 1 (11 points)
    Nov 18, 2013 5:19 AM in response to Octaviofb

    That's exactly it! I've just recently noticed that issue with the duplicates having the recipient's name, respectively mine.

    Although I'm quite relieved that this is not caused by a failed configuration on my part, it does not stop being anoying nonetheless.

    As you said, I really hope that Microsoft will fix this soon—it makes using Mail paineful. (Or will they?)

  • by Trinity22,

    Trinity22 Trinity22 Nov 18, 2013 12:05 PM in response to Valedictorian
    Level 1 (0 points)
    Nov 18, 2013 12:05 PM in response to Valedictorian

    Still why is it not happening when sending from the iPhone? ;-)

  • by woodstocknick,

    woodstocknick woodstocknick Nov 18, 2013 1:22 PM in response to Trinity22
    Level 1 (0 points)
    Nov 18, 2013 1:22 PM in response to Trinity22

    It doesn't happen on the iphone because ios devices connect via EAS/Exchange, which leaves it up to the device to save sent messages. When you connect via IMAP, Outlook/Hotmail saves a copy of the sent email on the server. This is left over from the days when they only had POP for desktop connections.

    Either Microsoft has to give us the option to turn this off on the server side or Apple needs to give us the option to stop OSX Mail from saving sent messages onto the server.

  • by Mr Tomness,Helpful

    Mr Tomness Mr Tomness Nov 28, 2013 4:02 PM in response to woodstocknick
    Level 1 (5 points)
    Nov 28, 2013 4:02 PM in response to woodstocknick

    Just wanted to try to draw some attention, I am also having this issue, and despite being able to de-select the "store sent messages on the server" button, this is not a good fix, as it thn removes my sent messages from the Mail application so i cant search my sent mail (something i often need to do).

     

    Apple please help find a solution for this!!

  • by Eric Root,

    Eric Root Eric Root Nov 29, 2013 1:38 PM in response to Mr Tomness
    Level 9 (71,578 points)
    iTunes
    Nov 29, 2013 1:38 PM in response to Mr Tomness

    Apple doesn’t routinely monitor the discussions.

     

    Send Apple feedback. They won't answer, but at least will know there is a problem. If enough people send feedback, it may get the problem solved sooner.

     

    Feedback

  • by DsMalka,Helpful

    DsMalka DsMalka Dec 14, 2013 10:31 AM in response to Valedictorian
    Level 1 (5 points)
    Dec 14, 2013 10:31 AM in response to Valedictorian

    I had the same issue with Outlook for Mac and was able to fix it. I went to Outlook/Preferences/Accounts, click on the account and then click on the advanced button at the bottom right. Click on the Folder tab and then make sure "Don't store a copy of sent messages" is checked. Save.

     

    That fixed my problem. Hope it helps.

  • by Jontypaine,

    Jontypaine Jontypaine Dec 19, 2013 6:43 AM in response to Valedictorian
    Level 1 (0 points)
    Dec 19, 2013 6:43 AM in response to Valedictorian

    Hi all,

     

    This was bugging me too but luckily found the fix today. In the Mail Preferences for the Hotmail IMAP account simply set the Outgoing SMTP server to None. The messages still send out but are no longer duplicated. As it is using IMAP I assume it does not require SMTP.

  • by Csound1,

    Csound1 Csound1 Dec 19, 2013 10:31 AM in response to Jontypaine
    Level 9 (50,511 points)
    Desktops
    Dec 19, 2013 10:31 AM in response to Jontypaine

    Imap is for incoming mail, SMTP is outgoing.

     

    Whatever you did it was not what you think, no SMTP server means no mail will send.

  • by hymced,

    hymced hymced Jan 7, 2014 2:31 PM in response to Octaviofb
    Level 1 (0 points)
    Jan 7, 2014 2:31 PM in response to Octaviofb

    Indeed, as Octaviofb underlines it, the problem also comes with Sparrow Mac with an Outlook.com account configured with IMAP. So there is definitely something wrong with how Outlook handles the new IMAP service...

     

    To be continued !

  • by hymced,

    hymced hymced Jan 8, 2014 5:30 AM in response to Octaviofb
    Level 1 (0 points)
    Jan 8, 2014 5:30 AM in response to Octaviofb

    I have find something. I think when using outlook.com with IMAP, even if you configure your account in your email client so that no copy will be put in the "Sent" folder, the IMAP service of outlook.com will make a copy. That's the bug of outlook.com IMAP.

     

    SPARROW

     

    Unfortunately, Sparrow will automatically put a copy in the "Sent" folder you have configured in the settings. That's why you get a duplicated copy in your "Sent" folder. And there is no way to disable this feature in Sparrow. And there is no way to use another SMTP than the Outlook.com one to avoid that bug either.

     

    MAIL.APP

     

    The problem is the same with Mail.app, you will have to deactivate the copy in the "Sent" folder IF USING OUTLOOK.COM SMTP (let's call this OPTION 1)

     

    You can also keep the copy feature activated and use another SMTP, smtp.gmail.com for instance (let's call this OPTION 2)

     

    But either way, you will have to check the "Use this SMTP server only" in your outlook.com account settings. Indeed, if you don't, you may have some problems.

    For example, let's say you use OPTION 1. If you send an email and if for some reason outlook.com SMTP isn't available, the email will be sent with Gmail SMTP. But since you have deactivated the copying feature, you will get no copy in your "Sent" folder !

    Conversely, with OPTION 2, you might get a duplicated copy if Gmail SMTP isn't available and your client use outlook.com SMTP.

     

    OTHER EMAIL CLIENTS (AIRMAIL, etc.)

     

    To fix that 'duplicated sent copy bug' with any other clients when using oulook.com IMAP, you will just have to make sure your client offers the possibily to disable the copying of sent email in the configurated "Sent" folder for your outlook.com account only (if you use multiple email accounts with your client, otherwise you don't need this last exclusive character)

     

    Note: iPhone mail client works properly with Outlook.com because it has native Exchange ActiveSync support, so it is not using IMAP to copy the sent email in the corresponding folder on the server.

    Note 2: Airmail 1.3.1 (current stable version) is compatible with Microsoft Exchange Servers, but not with Microsoft Exchange ActiveSync (EAS) which is the Exchange protocol used by Outlook.com. So at this time, Airmail 1.3.1 is only compatible with outlook.com IMAP and POP.

  • by hymced,

    hymced hymced Jan 8, 2014 5:35 AM in response to Valedictorian
    Level 1 (0 points)
    Jan 8, 2014 5:35 AM in response to Valedictorian

    I may have something interesting for you here: https://discussions.apple.com/message/24428593#24428593

  • by hymced,

    hymced hymced Jan 8, 2014 6:33 AM in response to hymced
    Level 1 (0 points)
    Jan 8, 2014 6:33 AM in response to hymced

    I forgot to say that when using OPTION 2, a copy will also be put in the "Sent" folder of the Gmail account used for the SSL identification with the SMTP server.

     

    So if your client has a unified inbox, it is completely normal if you have 2 copies in the unified "Sent" folder

  • by Valedictorian,

    Valedictorian Valedictorian Jan 12, 2014 11:34 AM in response to hymced
    Level 1 (11 points)
    Jan 12, 2014 11:34 AM in response to hymced

    Hi hymced!

     

    Thank you so much for your very detailed answer!

    I have—once again—tried to uncheck that little box which seems to be the heart of this issue only to notice that it doesn't actually say 'copy items to sent folder' (local), but 'store items on the server' (remote). Even though it's clear that I must leave that box checked for an IMAP account to be relevant, I did try to uncheck it to see what would happen, but it was (obviously) to no avail.

    I do use 'smtp-mail.outlook.com' only.

    Anyway, as I understand, there is little that one can do if the problem comes from Outlook.

    Should you find a better solution, I would be very happy to read about it!

  • by sparkle100,

    sparkle100 sparkle100 Jan 13, 2014 1:40 AM in response to Valedictorian
    Level 1 (0 points)
    Jan 13, 2014 1:40 AM in response to Valedictorian

    Hi all!

     

    If anyone finds a fix for this I would be grateful to hear about it!

     

    I purchased a macbook pro at the weekend and eventually managed to set my hotmail account up using IMAP and the 'smtp-mail.outlook.com'  for sending (after a number of failed attempts at being able to send mail).

     

    Once I finally set up mail to send, I started getting duplicates of all sent items.  Slightly frustrating but it would appear there is no simple fix for this yet.

     

    I assumed it would be so much easier to set up seeing as my iphone and ipad work so well!

     

    Thanks

  • by Octaviofb,

    Octaviofb Octaviofb Jan 13, 2014 10:15 AM in response to Valedictorian
    Level 1 (0 points)
    Jan 13, 2014 10:15 AM in response to Valedictorian

    Hello everyone.

     

    I see a lot of people have been having the same problem, and as far as I know Outlook.com still doesn't fix it. However, I am using another application to acces my email, after the issues with Mail and Sparrow. It's called Airmail, I believe it is in the Mac Store with version 1.2, I am using version 1.3 Beta. Not only it is a great app, it also fixes the double message in the sent folder that we have been discussing, I have been using it for a few months now and I can send email from my Outlook account and it shows only one copy in the Sent folder.

     

    I didn't do any special setup for this to happen, the program chose the right settings from the beginning, the only thing I would be carefull about setting the Outmail mail with the app is to be careful and use outlook.com in your email address instead of hotmail.com, the first one chooses the IMAP settings, the second one uses POP. Hope this helps, cheers everyone.

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