Thanks Lyndon, sorry about the delay in replying, day job got in the way. I wondered if the iCloud was troubled by other devices that might be involved and maybe I needed to get my MBP and iPad together with the desktop iMac and make sure all 3 are saying the same thing - but actually if I send email from the iPad or laptop, that appears ok in my sent list on the iMac ... it's just stuff I actually send from the iMac itself which doesn't get put in sent mail. Sub-accounts for other people work fine, but they have had the "keep sent mail on server" box checked all the time from way back. Still investigating.
Ive got the same problem and I found out that the problem was that on iCloud mail Web Interface! To get your email in the sent items once you send it... You have to go in the mail interface on icloud.com go to the settings gear > preferences > General tabs just check Save sent messages in: option. Once it's checked you have now your emails in the sent items folder.
I have done an extensive search but cannot find the answer to my query. I have been a long time user of apple’s email service and thus have an @firstname.lastname@example.org and an @icloud.com email address. Recently icloud has been playing up and is no longer storing my sent emails in the sent email file but is creating a smart “Trash” folder with a “sent Items” folder in that and this is where my sent items are coming up. I have gone into the preferences as above but it's not working!
This is not only annoying but is also mucking up my ability to sync properly with Postbox
Does anyone know what on earth is going on?
I'm sorry you're having problems; I haven't progressed this.
I never got round to working through it all on all my devices. As a good IT person in my day job I would be more keen on experimenting if I could secure the situation as it is, i.e. if I could back up my email stuff locally on a disk, in case I mess things up.
I might have another look if I get the chance and if I find anything out I'll post it.
I am currently running Mail.app on ML.
My Mail.app and iCloud webmail settings were already congruent with those recommended regarding saving a copy of the Sent emails [Store sent mail upon the iCloud server].
Despite this being the case, I have found that Sent messages were not been getting saved reliably in Mail.app or upon the iCloud webmail interface.
Some did get saved though - rather odd.
I don't want to call my reported email problem as fixed but it seems hardly coincidental to me that once I had chosen to unflag Store deleted messages [Trash section] upon the iCloud mail server that such messages as were sent form my two iCloud addresses messages began to be saved reliably.
Surely this is indicative of some underlying misconfiguration with the iCloud server itself as Trash messages clearly aren't Sent messages and yet messages only began to be reliably saved once I had chosen to unflag Store deleted messages. As previously stated, I already had my mailbox behaviours set to Store Sent messages upon the iCloud server, but this proved to be of no avail until I chose to unflag Store deleted messages.
See attached picture for Mailbox Behaviours.
I know this is a relatively old thread but I stumbled onto it and thought I'd share what I found while poking around. I was have the issue that when I sent mail from the iCloud web interface it did not show up in other places such as my phone or my email program on my PC.
When I checked the preferences, lo and behold my default address being used to send (under the "composing" tab) was the @icloud.com instead of @me.com (I have only ever used or given out the @me.com address). I changed it to @me.com and tested an email, works fine now.
Hope this helps someone!