MAC Mail not saving all sent items

Thank you dmt1. These was frustrating me immensely and I tried many things including the main suggestion provided by google of

In the IMAP Path Prefix text box, type INBOX. Make sure you capitalize the entire word. ...

All that did was remove all my side folders! Then I saw your reply and hey presto there are all my sent items! Thanks again!

I have a new MacBook running OS X Yosemite (10.10). I had the same problem and one of the notes prompted me to check my "Mailbox Behaviors" where I noticed that "Store sent messages on the server" was checked. I unchecked this box and the sent log works. I don't know where this server is (I went and looked in my provider's sent mail but it wasn't there).

It's mind boggling that after almost 44 pages and nearly 5 years I can report that this is STILL an issue. I first noticed this when I moved to Mavericks. I recently upgraded to El Capitan (v10.11.4 w/ Mail v9.3) primarily in hopes that it would have finally fixed this mail problem. No joy.

As those who've bothered to read the thread know, it's an issue where IMAP sent mail is occasionally not saved to the server, but the addressee confirms the message received. Though some report it happening with a all types of mail, it usually seems to be related to mail with attachments. Some have "solved" it by changing their preferences to only save mail locally on their machine. This defeats the purpose of using an email solution that is designed to sync across platforms. I'd be curious to see if any of the early posters who identified the actual issue have seen it resolved. I certainly have not.

The only new thing I've seen that is hopeful, is that with El Capitan, where previously a piece of outgoing mail mail would be lost with no trace of it having been sent, I just today had the lost sent message show up in a newly generated "On My Mac" folder under the Sent hierarchy. I had not changed any settings in Mail preferences, and the account was still configured to store outgoing mail on the server's Sent folder. All I can hope, is that if there is an issue with the server handshake that saves mail to the Sent folder, that now Mail has a failsafe that at least catches the message and dumps it in a local folder. At least that would be something. Crossing my fingers.

I've had this infuriating issue, exactly as you describe, consistently for years. The best solution is to save every mail as a draft, and check it has been saved, and then hit send without altering it further.

As you say, the mails that give most troubles are ones with attachments. I often find, if the draft won't save, that it's best to go onto my webmail interface and do it from there. Which is clunky. If it's a simple text email I can finish it on my iphone, which sends solidly.

The issue didn't change one bit when my provider (virginmedia) went from a gmail back end to a proper SMTP back end.

It initially appeared to have been fixed in El Capitan. That was advertised as having the biggest changes to mail.app for years, and also one of the features is said to be that it works more reliably when the server connection is flaky.

But now here I am in El Cap 10.11.4 and it's back. Sigh.

Paul

Have you found that on El Capitan if the sent mail does not show up in your SENT folder for the associated IMAP account that Mail is generating a local "On MY Mac" folder under sent where it ends up? This has been the behavior for me since switching to El Cap.

I just today tried to send an email with a 2+MB PDF attachment. I watched it sit in the Outbox and then it disappeared. I got confirmation from a recipient that it was indeed received, but it was not in the SENT folder for the IMAP account. Low and behold, rather than fully disappearing as with Mavericks, it was in the "On My Mac" folder. I simply dragged the message from that folder to the correct IMAP SENT folder and all is well.

It's still not fixing whatever the underlying issue that's been going on for 5 years for a significant group of users, but at least it's some sort of failsafe with my setup. Don't know how reliable it is, but I've been confirming outgoing mail with every send since the upgrade to El Cap. So far 2 for 2 missing Sent messages (both with larger attachments) were routed this way.

I've just encountered these issues. So far to fix the problem in Mail Accounts, mailbox behaviours un tick store sent messages on the server. Unchecking this now stores sent emails on my mac.

That doesn't "fix" the problem, it avoids the problem by disabling a feature that is not functioning correctly in Mail.app. Hope you enjoyed the 44 page, 5 yr old thread documenting this. I know I did.

I'm tired of sending important files, only to discover there's not a copy in the sent folder.

And now I find a 5-year old thread and Apple STILL hasn't fixed the problem?!

I searched the On My Mac section and it's not there. I'm going to need to start copying myself on all emails to ensure I have a copy?!

This is ludicrous.

Has your workaround been consistently reliable? Please report back when you have a chance. Thanks!

Seriously - this is STILL not fixed by Apple after FIVE YEARS????

Unbelievable... Truly...