MAC Mail not saving all sent items

We should tell that to Steeve Jobs !!! He would'nt be proud of it !!!

Let's tell him...he's maybe in Icloud and will come down to kick some *** in that arrogant corporation.

Same issue here and still no solution. None of my sent emails are saved to the selected 'sent items' folders. All settings have been double checked and are correct (Yes, I have checked the option 'save to server' and the Mailbox menu 'use this mailbox for' option). Thunderbird has no problem saving sent emails in the correct folder. This must be an Mail application problem, NOT a problem with my ISP as Apple claimed... I just updated to Mountain Lion and problem still persist. I don't understand that in 1969 man walked on the moon, but in 2012 it seems impossible to keep a copy of a sent email in the correct folder 😠. Come on Apple! A little help here please!

Their has been a lot of misunderstandings and confusion with settings etc, as mentioned in previous threads. However having spent some time talking to our hosting provider and testing with various mail clients, here is my understanding of whats going on and causing this issue.

Firstly I don't think this is directly an Apple Mail issue and believe their is some other services at the OS level that Apple Mail uses when sending messages. In our experience we have had the same problem with both Apple Mail and Microsoft Outlook for Mac. Thunderbird seems to work ok. It May be that Apple Mail and Outlook use the same system level service when sending mail and that maybe Thunderbird has its own service built in which could explain why it seems to work ok.

Secondly after speaking to our hosting provider who have acknowledged that their 'Intrusion Detection & Prevention' (IDP) system in their data centre is blocking the connection when our email client attempts to store the sent message into the 'Sent' folder. We have done some tests and they have monitored their logs.

Details on the error from our hosting provider;
IMAP:EXPLOIT:CMD-FORMAT-STRING has been detected from xx.xxx.xxx.xx/xxxx to xxx.xxx.xxx.xx/xxx through policy 324 1 times.

Apparently the IDP system monitors for non-standard or erroneous commands to the server, emulating the activity which would be generated by an attacker attempting to abuse an exploit in the IMAP server. And it may be that Apple is using non-standard commands which is tripping the system to block the connection.

Unfortunately I don't think their is a solution. Apple have told us to setup an IMAP account with Google Gmail and test that…which works fine. Obviously Google use different security in their data centres. Apple will blame the hosting provider and most hosting providers who have invested in IDP systems in their data centres will not risk disabling them for a few Mac users who are experiencing this issue.

The only way I can see going forward is to either change to Thunderbird, Sparrow or switch to a different hosting provider and hope that their security systems are different.

I believe that hosting providers such as RackSpace use the same IDP as our service provider and would explain why some of the users in previous threads state RackSpace as their hosting provider.

I had a similar problem. My situation was like this: yahoo mail account, google mail account no.1 and google mail account no.2 added to Mac Mail app on MBA2012, OS 10.8

Google mail accounts were fine.

But emails sent from the Mac Mail app using the Yahoo Mail account were not being saved anywhere. Problem was intermittent initially but then it became permanent in the past couple of days.

My problem seems to have been fixed by selecting the Sent folder that appears in the folder list for the Yahoo Mail account and then going to Mailbox -> Use this Mailbox for-> Sent.

Of course, store sent message on the server was already selected but without the step above it was still not storing.

So now messages sent from the Mac Mail client using the Yahoo mail account can be found in the Sent (paper airplane) in Mac mail and in Web Yahoo Mail in the normal Sent folder (so not in a Sent Messages folder that is in the folder list).

Also, to confirm, messages sent from the Mac Mail client using the google mail accounts suffer nothing from action above and will show up in the Web Google accounts as normal in Sent folder.

I'll post back if I notice erratic behaviour with Sent messages but it seems to be working now.

Note1 : Yahoo is set up as IMAP account so it's possible that the above is valid solution for other (non-yahoo) IMAP accounts.

Note2: Yahoo Mail had been working / upgrading their servers in the past few days, including today (it was actually down for a while) so the best idea is to delete the account and add it again to Mac Mail.

I actually deleted all 3 accounts from Mac Mail, quit Mac Mail, restarted Mac, started Mac Mail again, added the accounts, did the change mentioned above and then it worked.

Note3: I also changed the port in the the Edit SMTP Server List to 465 because that's what Yahoo officially recommends for Yahoo Mail but I do not think that has any bearing on the issue of sent mails being lost (possibly makes connection to Yahoo Mail more consistent if Yahoo Mail server only responds on that port)

Note4: Adding INBOX to IMAP Path prefix totally screwed things up for me (possibly because I have more than one account added to Mac Mail) - I wasn't getting any emails.

Note5: I have 2 aliases for the Yahoo Mail account and they are added to Mac Mail app and the fix above works fine for them as well.

Good luck

ag777

This explanation makes sense and made me look further. It seems you're right Chris, thank you for this. The problem was that my ESP (email service provider) didn't grant full acces/privileges to Apples Mail application to alter or write in email folders. This means Mail couldn't copy a sent email to the 'Sent' folder on the IMAP server. I just switched to another provider, which fully supports IMAP. So problem is solved.

Unfortunately I don't think their is a solution. Apple have told us to setup an IMAP account with Google Gmail and test that…which works fine. Obviously Google use different security in their data centres. Apple will blame the hosting provider and most hosting providers who have invested in IDP systems in their data centres will not risk disabling them for a few Mac users who are experiencing this issue.

I think this is not true. I have the same problem, and this is with Yahoo Mail. Considering it is a marquee partner of Apple (they have special treatment within Mac mail), you would think there would be no issues, or it would be on apple/yahoo to make sure this works, not some third party. It also means I have no choice in whether to use another mail client -- Yahoo isn't likely to change anything for me (a non-paying customer). I suppose I could move to gmail, but I would not have much confidence it would fix the problem -- and then I have wasted all kinds of time updating everyone of my new address. I would not be surprised if the same thing happens with gmail, just less frequently.

I also have issues where mac mail sometimes *omit* portions of a message. For example, a message which contains an attachment on my iPhone does not in mac mail. Turns out it's because mac mail mysteriously deleted in its local copy the portion of the message with the mime header. See here: https://discussions.apple.com/thread/4157249. This happens probably 1-2% of the time. Again, in Yahoo Mail.

I really love the mac mail UI, Apple has done a great job (as usual), but this corruption of data makes me really concerned about continuing to use it, esp. for business.

Just an update and you're right some of the posts here do not understand the issue.. Now even after upgrading to mountain lion I still lose random sent messages.. do not appear in the server sent nor in macmail sent, but the recipient receives it... I am also a rackspace client.. Apple is really falling down on this

Yep, it just happened to me THREE times this week. I am looking for a job, and it's really a problem when you have no record of an inquiry you sent to a prospective employer. I have Mountain Lion and same thing...no solution. I guess I'll have to get a different mail program. Disappointing....

Hi All:

I just got MailHub for Lion and it has a bunch of cool features for organizing my email plus asks me when I send a message where I want it filed.

I have 3 email addresses (1 personal, 2 business related) and so this has helped me in a lot of ways and seems to have bypassed/solved/avoided the missing sent mail problem so far.

I got it through MacUpdate promo.

Hope this might help someone else!

Karen

THANK YOU! This was driving me nuts. I also have a yahoo account that wasn't playing nice. This is great! It's working now.

I seem to be having this exact problem, but I could swear it only started happening after I upgraded to Mountain Lion (10.8). I hoped their would be a 10.8 update coming that would fix the problem, but from this thread, it appears the issue has been around long before ML was released.

I have a small twist with my symptoms:

• Small messages do seem to get properly (and immediately) saved to "sent" folder
• Any message longer than about 1-2 lines of text is not saved to "sent". The "mail activity" window indicates Mail.app is trying to save to "sent" folder for about 15 seconds, then gives up (silently)

I tried downloading Thunderbird, and connected to same IMAP account. It seemed to save to the "sent" folder properly.

However, I also downloaded the PostBox (postbox-inc.com) mail client for Mac (30-day trial), and it exhibited the exact same behaviour as Mail.app: small (one-line) messages are delivered and saved to "sent" folder, but anything longer does not get saved to sent. It actually fails with an error that "the message was sent properly, but could not be saved to your sent folder".

Only workaround I found is to change the "sent" folder to be local. This is not acceptable because the sent messages are not visible on my iPhone/iPad (which is one of the main points of using IMAP in the first place).

To all posters. I, and others, have posted several times reporting that Apple said that the Mail group is looking at this issue. This cannot be true or they would have fixed it long before now. They do not read or respond to this discussion group. The only thing that may get their attention is for all of you to log a service call on your AppleCare warranty plan. If anything, sychronization problems are getting worse with Yahoo IMAP servers. I think the intrustion protection suggestion previously posted as a likely cause is a very good one. My Android phone has no such difficulty. I love Apple and Macs, but not fixing this problem is inexcusable and gives them a black eye in my book. I like the simplicity and features of Mac Mail, but it is really annoying and time-wasting when it also can't synchronize or read mail without popping us a password window instead of retrying the one in keychain.

My wife gets this problem on her Air Book but I don't get it on my MacBook. I've tried various attempts to fix it but no joy yet. There do seem to be a lot of Air Book users on this thread. Any possibility that this is the defining common feature?

Either way it is inexcusable: a basic failing that you'd associate with freeware and not a branded package.

I see the same problem. Sometimes email sent from my iCloud account shows up in sent items; sometimes not.

I'm on a Macbook Pro so it's not just MacBook Air users who see this problem. Anyway I don't think the problem is caused by the mail client, because it's reflected in the web-based version of iCloud email.

Such a serious failure should not be allowed to persist, especially not by Apple.

Nice work Apple. I talked my wife into switching from windows to mac. So far the things she relies on the the comuter most heavily for seem to suck on the iMac. After loosing important sent messages and trying to deal with other short-commings, she asked me if we could please buy a new PC. Lovely. Wish we could say we were feeling the love for Apple...

Step one: buy an Apple comuter. Step two: buy all the software you used to use your PC for in Mac OS. Step three: Stratch head and wunder why you made the switch...