Sent items show twice on MAIL (IMAP)

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.

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.

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.

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.

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.

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

Two other workarounds.

- Ignore it, it is only cosmetic.

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

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.

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. 😉

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.

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.

Please don't tell me what you think I mean, you are wrong.

applicability wrote:

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.

There is no such thing as an Imap Sent folder, that would be the SMTP folder (Imap is incoming)

But do as you wish.

OK. You're right, I have no idea what you meant. And I just stopped caring.

For anyone else who is here in the interest of productively sharing ideas rather than simply trolling, here is what I am talking about:

That Sent folder at the bottom will continue to contain all of your Outlook.com Sent items and they will be synchronized, excuse me, "copied back and forth to" your Outlook account automagically via IMAP.

Or you could map the Outlook sent folder to the Mail sent folder and have all the sent mail in one folder, where it should be without disabling the server save in Mail.

To Map a default folder that's on IMAP, select the IMAP folder.

Under Mailbox in the Menu bar, select use this mailbox as.....