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 jasse17,

    jasse17 jasse17 Mar 27, 2014 10:10 AM in response to Valedictorian
    Level 1 (0 points)
    Mar 27, 2014 10:10 AM in response to Valedictorian

    I found a setting on outlook.com which fixes this.  If you log into the web interface, go to the options page, and select "Saving sent messages" under the Writing Email section, you can turn the server side saving off, and your mac mail client will still save the message.  Hope this helps!

     

    Turns out this doesn't work. Sorry!

     

    Message was edited by: jasse17

  • by woodstocknick,

    woodstocknick woodstocknick Mar 27, 2014 10:13 AM in response to jasse17
    Level 1 (0 points)
    Mar 27, 2014 10:13 AM in response to jasse17

    This does not work. If you notice, it says messages will still be saved if you connect externally (i.e. with a mail client)

    The problem is that outlook is saving messages in addition to mail.app.

    In my opinion, the even bigger problem is mail.app doesn't update deleted or moved messages to the server until you close the app. You'll delete a message and it's still on the web and mobile until you close mail.app.

    That's why I'm using Airmail. It's available on the App Store.

  • by svkrzn,

    svkrzn svkrzn May 22, 2014 11:59 AM in response to woodstocknick
    Level 1 (36 points)
    iPhone
    May 22, 2014 11:59 AM in response to woodstocknick

    Have been using outlook.com for one month and just have noticed now that weird problem of duplicate sent items... What a pity...

  • by Csound1,

    Csound1 Csound1 May 22, 2014 12:03 PM in response to svkrzn
    Level 9 (50,876 points)
    Desktops
    May 22, 2014 12:03 PM in response to svkrzn

    Yes, it's a known issue with Outlook.com, yu'll have to wait for MS to fix it.

  • by D.R.C.,

    D.R.C. D.R.C. May 28, 2014 7:48 PM in response to svkrzn
    Level 2 (162 points)
    Apple TV
    May 28, 2014 7:48 PM in response to svkrzn

    I too have recently starting using outlook.com with Apple Mail, and encountered duplicate messages being saved in my Sent folder.

     

    Here's a fix that worked for me. I had been using smtp-mail.outlook.com as my SMTP server, per Microsoft's setup instructions.

     

    I changed Mail's settings to smtp.live.com:587  (thanks to this article at about.com):

    http://email.about.com/od/Outlook.com/f/What-Are-The-Outlook-com-Smtp-Server-Set tings.htm

     

    My outgoing messages get accepted for delivery by the live.com smtp server and sent on to the destination address. However, as they pass through live.com, they don't get saved into Outlook's server-side /Sent folder.  Locally, Apple Mail saves each sent message into its Sent folder, which then gets synced by imap into the server folder.

  • by Csound1,

    Csound1 Csound1 May 29, 2014 3:10 AM in response to D.R.C.
    Level 9 (50,876 points)
    Desktops
    May 29, 2014 3:10 AM in response to D.R.C.

    D.R.C. wrote:

     

    I too have recently starting using outlook.com with Apple Mail, and encountered duplicate messages being saved in my Sent folder.

    This issue was first noted by Microsoft back in Nov 2013, they still have not fixed it but promise that they will (google it), maybe another 6 months will be enough for MS to figure out the problem, maybe not, it's MS after all.

     

    I changed Mail's settings to smtp.live.com:587  (thanks to this article at about.com):

    http://email.about.com/od/Outlook.com/f/What-Are-The-Outlook-com-Smtp-Server-Set tings.htm

    Why are you scanning articles, MS are the authority on their own email systems, asking them is usually the best way to get their settings.

  • by D.R.C.,

    D.R.C. D.R.C. May 29, 2014 4:23 AM in response to D.R.C.
    Level 2 (162 points)
    Apple TV
    May 29, 2014 4:23 AM in response to D.R.C.

    D.R.C. wrote:

     

     

    Here's a fix that worked for me. I had been using smtp-mail.outlook.com as my SMTP server, per Microsoft's setup instructions.

     

    I changed Mail's settings to smtp.live.com:587  (thanks to this article at about.com):

    http://email.about.com/od/Outlook.com/f/What-Are-The-Outlook-com-Smtp-Server-Set tings.htm

     

     

    Alas, this worked yesterday, but the duplicate messages (filed in the Sent folder) recur today.

     

    I've abandoned the use of Microsoft's SMTP servers and am using another server to send my mail. No more duplicates.

  • by Csound1,

    Csound1 Csound1 May 29, 2014 4:41 AM in response to Octaviofb
    Level 9 (50,876 points)
    Desktops
    May 29, 2014 4:41 AM in response to Octaviofb

    That's right, you have disabled saving a copy on the server, so sent mail will not sync correctly with other devices (iPhones etc) but will look correct on your Mac.

  • by D.R.C.,

    D.R.C. D.R.C. May 29, 2014 8:10 AM in response to Csound1
    Level 2 (162 points)
    Apple TV
    May 29, 2014 8:10 AM in response to Csound1

    I'll just clarify that I  did not disable saving a copy on the saver. That option is (and always has been) enabled on Mail's settings for my Outlook account.

    My sent mail now (a) gets saved in Mail's Sent folder, (b) gets synced to the Sent folder on the Outlook server and (c) gets synced to my other devices (iPhone). No duplicates.  It's all working as desired, across all my devices.

     

    However, I should point out that my solution may not be generally applicable, as it requires use of a different SMTP server. I'm using one from another service provider, not Microsoft's. That's why  duplicate messages don't appear in my sent folder.  Most Mail.app users who are afflicted by the duplicate messages probably have access to an alternate SMTP server (from their ISP, from Gmail, etc).  That's a viable workaround until Microsoft resolves the issue.

  • by Csound1,

    Csound1 Csound1 May 29, 2014 9:34 AM in response to D.R.C.
    Level 9 (50,876 points)
    Desktops
    May 29, 2014 9:34 AM in response to D.R.C.

    Yes, one way to deal with Outlook.com's Sent mail issues is not to use Outlook,com for sending mail,

  • by peter_watt,

    peter_watt peter_watt May 30, 2014 12:07 PM in response to D.R.C.
    Level 3 (910 points)
    May 30, 2014 12:07 PM in response to D.R.C.

    Two other workarounds.

    - Ignore it, it is only cosmetic.

    - Use Airmail app instead of Mail. (My workaround, as I like outlook.com).

  • by peter_watt,

    peter_watt peter_watt Jun 1, 2014 9:40 AM in response to peter_watt
    Level 3 (910 points)
    Jun 1, 2014 9:40 AM in response to peter_watt

    peter_watt wrote:

     

    Two other workarounds.

    - Ignore it, it is only cosmetic.

    - Use Airmail app instead of Mail. (My workaround, as I like outlook.com).

    Hmmm,  Airmail, still does it, just hides it better. 

  • by applicability,

    applicability applicability Jun 7, 2014 10:13 AM in response to Valedictorian
    Level 1 (0 points)
    Jun 7, 2014 10:13 AM in response to Valedictorian

    Here's another idea I don't think anyone has mentioned yet: prevent Mail from saving copies of your Sent messages and let Outlook handle them entirely, as follows:

     

    Go to your Outlook Mailbox Behavior settings, uncheck "Store sent messages on the server" and also set the "Delete sent messages when" option to "One day old". Then also check that in Account Information the Outlook.com server is set as the SMTP provider and the checkbox "Use only this server" is checked.

     

    I believe the only real downside to this is that you won't see a difference until the next day, when the duplicates should be automatically deleted for you. Please test this at your own risk.

  • by Csound1,

    Csound1 Csound1 Jun 7, 2014 10:15 AM in response to applicability
    Level 9 (50,876 points)
    Desktops
    Jun 7, 2014 10:15 AM in response to applicability

    applicability wrote:

     

    I believe the only real downside to this is that you won't see a difference until the next day, when the duplicates should be automatically deleted for you. Please test this at your own risk.

    And that synchronization of Sent and Deleted messages will cease, little things like that.

  • by applicability,

    applicability applicability Jun 7, 2014 10:33 AM in response to Csound1
    Level 1 (0 points)
    Jun 7, 2014 10:33 AM in response to Csound1

    Csound1 wrote:

     

    And that synchronization of Sent and Deleted messages will cease, little things like that.

    I think what you mean is that the Outlook.com sent messages won't be shown as part of your unified Sent Mailbox, but rather as a separate mailbox under the name of your Outlook.com account in the folder list below.

     

    The actual synchronization with the IMAP Sent folder still happens though, so you can always go into that separate folder if you ever want to look at things you sent. Also, Mail is still smart enough to show your responses in the conversation view, even though they're not saved in its unified Sent folder.

     

    It's not exactly a "real" solution but it's the only one I've found that I can live with so far... especially since I've done time with both Sparrow and AirMail and came back unsatisfied with either.

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