Mail not saving large outgoing messages

i've recently noticed that when sending large outgoing messages (typically 10mb or more), mail sends but does not save the sent message. i'm using IMAP Gmail. everything else (ie, anything smaller) sends and saves fine.
anyone else noticed this/got a fix? i'm using mail 4.1 on OS 10.6.1, but i had trouble with mail in leopard where it wouldn't send large emails at all.

Yes I am having the exact same problem - email just disappears totally whilst being sent - nothing in drafts or sent items - the email has totally disappeared - very very annoying...
I am feeling very angry with Apple and things that should 'just work' that just 'don't work' any more - the whole OS is becoming totally unreliable - I'm seriously considering ditching this junk (after 3yrs of Apple purchasing) and going back to Windows - Apple are the most arrogant and uncommunicative company I have ever known...

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Mail not saving sent Exchange messages

Sort of an odd bug. Mail isn't saving messages from my laptop locally. It will save anything I send from my iPhone to the server and I can view them fine on my laptop in the sent folder. However, if I send it from my laptop, it will not save anywhere. Ideas?

Nevermind. I figured it out. I had migrated from an IMAP version of this particular account to an Exchange version. I was still listing the IMAP version of the account as the outgoing server. I changed that to the Exchange outgoing server and it's all set.

Mail not saving sent messages

I've noticed that Mail is not saving my sent messages. I started to notice this yesterday. It's very erratic though. Sometimes it does, sometimes it doesn't. I have the option selected in preferences to Store Sent Messages on the Server (my .mac account).
Any idea what is going on? I even checked my .mac Sent Mesages folder using WebMail and they're not there either.
John
PowerMac G5 Dual 2.3 Mac OS X (10.4.2)

You're welcome.
With a .Mac or IMAP type account, you can save Drafts, Sent, Trash and Junk messages on the server instead of locally on the hard drive.
Messages in a .Mac or IMAP type account's Inbox mailbox remain on the server until deleted from the account's Inbox mailbox or moved from the Inbox mailbox to a user created "On My Mac" mailbox or deleted from the server using webmail access.
You can also create additional mailboxes that will be stored on the server.
Messages in the account's Inbox mailbox and in any other mailboxes stored on the server are synchronized with the Mail.app and with other email clients.
With POP type accounts, received/incoming messages are downloaded by the Mail.app and by other email clients. You can choose when messages are deleted from the server when downloaded by the Mail.app and by other email clients but you cannot store Drafts, Sent, Trash or Junk messages on the server or create any additional mailboxes that are stored on the server.
A .Mac or IMAP type account is beneficial for those who access their email account with multiple computers and want to keep all mailboxes for the account synchronized on each computer.
For example, you have a Desktop at work but also travel with an iBook or PowerBook. If you have a .Mac or IMAP type account and select save Drafts, Sent, Trash and Junk messages on the server in Mail on both Macs, all mailboxes for the account will be kept synchronized in Mail on both Macs. Messages sent with the iBook when traveling will be available on the Desktop Mac in the office and vice-versa.

Why does Mail mark all my outgoing messages as "junk?"

I recently upgraded from OS 10.4.4 to 10.5.5 on both my iMac and PowerBook & now Mail marks all my outgoing messages as "Junk."
I reset my junk mail preferences--and manually marked all my outgoing messages as "Not Junk Mail"--but nothing changed.
Is anyone else having the same problem?
Can anyone offer a solution?
Does anyone else think it's strange that this is even possible? Shouldn't administrators' messages always be marked "Not Junk Mail" by default?
Help!!!
iMac Mac OS X (10.4.5)

I recently upgraded from OS 10.4.4 to 10.5.5
Mac OS X 10.5.5? Wow! I thought it would be 1 year or so until Mac OS X 10.5 ships and you've already installed its .5 revision! What kind of Developer Program are you a member of?
Sorry, couldn't resist!
Now, seriously, you're certainly not alone. I've seen quite a few threads about this very same issue here. Just search for "junk" and "sent" in this forum:
http://discussions.apple.com/search.jspa?threadID=&q=junkANDsent&objID=f753&dateRange=last90days&userID=&numResults=15

Apple mail not showing all the messages?

In Apple mail, for my icloud account, I have some mailboxes which show the wrong number of messages, it shows too few.
As an example, a mailbox contains 150 messages, but apple mail reports there are only 146.
I rebuilt the mailbox and let apple mail do its thing. In the activity window I can see there are 150 messages. Yet, once apple mail has finished rebuilding the mailbox, it still tells me there are 146 messages. What's going wrong? Why would apple mail not show all the messages while in the activity window it clearly shows it knows there are 150?

Solved!
This was too weird to be real. Apple mail does not show messages it believes to be duplicates, and buy, does it make big mistakes in deciding what are duplicate messages and what not! Some of my mailboxes had over 100 "duplicates" not showing according to apple mail.
I found a solution thanks to this topic:
https://discussions.apple.com/message/18265121#18265121
defaults delete com.apple.mail AlwaysShowDuplicates
does yield an error in 10.8.2 ( Domain (com.apple.mail) not found. Defaults have not been changed. )
defaults write com.apple.mail AlwaysShowDuplicates -bool true
Does work brilliantly though!

Mail not saving IMAP drafts or outgoing messages

I've searched the HELP topics and have not seen how to solve this problem. I have multiple accounts set up in Mail; a couple are yahoo.com/sbcglobal.net accounts and a couple are through two different companies for which I work. Most of them are set up as POP accounts, and they are behaving properly. The problem is with the one that is set up as an IMAP account. It successfully sends and receives mail, but it will not save drafts or the outgoing mail. I realize I can blind-copy myself and have the messages saved as incoming, but I'd really like them saved as drafts and outgoing. Thanks for any advice!

Hi Dantedelg,
If you are having an issue with your MacBook Air's Mail application not saving the Sent mail, you may want to check your Mail Preferences under Accounts > your account > Mailbox Behaviors > Sent. What is the setting for Delete sent messages when: set to? You may wish to change this setting. See this article -
Mail (Yosemite): Set up Mail with your email accounts
Thanks for using Apple Support Communities.
Best,
Brett L

Mail not saving sent messages, not moving Junk messages

Hi everyone, I'm having a bit of trouble with OS Mail. I've set it up to use an IMAP account, and have set my preferences such that Mail should save all my sent messages in the Sent folder (I assume the Sent folder on my computer, not the one on my IMAP server). Regardless, neither my IMAP server's sent folder nor my computer's sent folder contain any messages that I've sent, and I have confirmed that these messages have in fact been received by the recipients (therefore successfully sent). I am unsure of how to resolve this issue, as there is no obvious setting change for me to persue. I just received this computer (new) a few days ago, so I wouldn't expect this problem to be due to disk maintenance/management, etc.
Also, I have noticed that Junk messages remain highlighted and in my inbox. I changed my prefs to have these messages be placed in my Junk Mail folder. Mail asked me whether I wanted to apply that preference to older messages marked as junk that have yet to be put in the folder; I indicated yes. Nothing happened, and the Junk Mail folder remained empty (until I manually moved the messages to it). Any ideas?
I have searched the forums for related issues and could only find problems that had an associated error message with it; my issue is different in that there are no error messages; Mail is simply ignoring my preferences. Thanks in advance,
Vic

In OS X Mail, this sent folder appears as a subdirectory
(sub "mailbox"?) under my "Inbox" mailbox along with
other folders that are mapped on my IMAP account.
This means you haven't set up your account properly. You probably should set Preferences > Accounts > Advanced > IMAP Path Prefix to INBOX, or something like that.
After putting the right string in the IMAP Path Prefix field, either the IMAP folders will appear somewhere else in Mail (i.e. not as subfolders of Inbox), or your problem will have already been fixed. Let me know what happens.
I should probably mention (just realized) that in my
account settings, my outgoing SMTP server is set to
be my ISP's server (which is different from my IMAP
provider).
I wonder if, by selecting "save messages on server"
I am saving these messages somewhere on my ISP?
Mail should still save the sent messages where you've told it to. It's Mail, not the SMTP server, that stores the sent messages. The SMTP server has no bearing on this, but it was a good idea to consider that possibility, nevertheless.
When I uncheck this option, perhaps my mail will
be stored on my local computer instead?
Yes, that's what would happen, but don't uncheck that option if you really want your sent messages to be stored on the IMAP server, or do it temporarily, so that Mail does at least save them somewhere until we fix the problem, but I believe I already know what the problem is.

Some sent mails do not appear/are not saved in "sent messages" and are lost

i work with mail and 4 different imap accounts. about every 15th sent email "gets lost". i.e. i can follow the sending process in the activity window, and i hear the sending confirmation tone. and, usually, the mails even reach the receiver. BUT, the mails do not appear/are not saved in the "sent messages" folder and are lost. this is very unsettling, as there seems to be no recognizable pattern. can anyone help, or should i change to "entourage"? big thanks for replies
Message was edited by: Bassolino

Hi Bassolino and David,
I, too, have had this intermittent issue and wonder if you had found a solution?
In the past 3 weeks, two messages have been sent from my mac mail account, using the mail application (the only apparent common factor being that both messages had iphoto attachments), the recipients have received them - only I do not have a copy in my 'sent' folder.
They are not stored on the macintosh server either...
I have not altered any settings and this intermittent issue has just emerged.
Any help from 'Top Users' would be welcome. Thanks.

Mail not saving sent messages (in the year 2015)

I recently switched from Entourage to Mac Mail (I know, I know) on my laptop running 10.10.1, but have been increasingly annoyed with Mail's inability to save Sent mail at random times. I use Mail with only ONE e-mail account (Comcast IMAP), and yet it often takes FOREVER to send an e-mail and then there is no record of it. This is causing me all sorts of problems professionally and personally. I started looking into this only to find that it seems to be a longstanding issue with no solution. Has anyone solved this? I am contemplating going back to Entourage, which is RIDICULOUS.

Have continued to look into this, and it looks like this affects IMAP accounts only. It sounds like you need to specify for Mail exactly WHERE it needs to save messages, even if you're only using one account, like I am. I found these directions on a site called Media Temple, and am trying them (I know some folks have said some of these options are grayed out, but I did have a Sent folder nested inside my Inbox that this process worked for). Will update here if this does not seem to solve the problem (it takes a while to test changes because this problem appears randomly).
Q: Emails sent in Mail do not appear in my Sent Folder, why?
A: When using IMAP, as we recommend for the Grid, Mail requires you provide a specific folder to save sent messages. Follow these simple steps to configure this:
Click and highlight the "Sent" folder for your account.
Click the "Mailbox" menu
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Choose "Sent"
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Mail not saving messages in Sent if previously in Drafts

This question was already posed several months ago but not really answered so I am trying it again.
I sometimes save a draft message in the draft folder only to send it later. Often it is the case that this previously saved draft does not appear in the Sent folder after being sent. I use IMAP settings and have four accounts running simultaneously. Other than in this case, mail is saved consistently in the sent folder.
Any help would be greatly appreciated.
Gerry

Thanks for discovering this issue being connected to drafts. I have trouble with this for a couple of months as well.
Since you assume it to be connected to "drafts", I suggest to deselect "Store draft messages on the server" for your IMAP-Account. I just did this for myself, to see if it helps, and can't give you results yet. Maybe you just wanna try simultaneously. I guess, the reason for our problem could me some messy communication between Mail and the server, where one party get's confused.
Greetings
Paul

Outlook for mac 2011 sent mail file too large error message

The synchronization of outlook with gmail is slowing down because there is a stuck message that appears to be too large.
Have tried to run a script i found out about to delete and it didnt work. I also went to Offline mode and sent myself an email so i could see the outbox and there is nothing there.
Suggestions appreciate.

Normanfrompalmyra,
Gmail does not have an outbox per se. While you are composing or writing an e-mail, it is automatically saved in the Drafts folder. After you hit send, a copy of the e-mail is saved in the Sent folder. So, you can look in both those folders.
If you are in Outlook, click on the Home tab, then look at the left side of the Outlook window. You should see a column on the left with each of the different e-mail accounts that you have set up in Outlook. At the top of this column are the four general folders: Inbox, Drafts, Sent Items, Deleted Items. Below that are folders for each e-mail account, under which you see the folder structure you created for each e-mail account. If you know which e-mail is causing the problem, look under Drafts, Sent Items, then Deleted Items for that e-mail.
Good luck,
Arbor Friend

Database mail not sending no error messages

SQL server 2008 R2
Database mail was up and running until sometime last week. It seemed to quit in the middle of a long list of emails. We had network issues at this same time that might have contributed to the issue.
Everything checks out ok today but I cannot send a test email. I do not see any error messages or 'db mail starting up' messages in the log.
I do see the Email in the sysmail_unsentitems view.
I do not receive any error messages.
I tried setting up a secondary account and that did not make a differnce.
I tried stopping the mail service with EXEC msdb.dbo.sysmail_start_sp and the query never completes. I canceled after > 5 minutes
I deleted many unsent and one retrying message from the queue. I see those actions in the log.
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KD

Have you worked through the troubleshooting steps in the following BOL Topic to validate that the external executable is activating, and the queue status is correctly returning RECEIVES_OCCURRING:
http://msdn.microsoft.com/en-us/library/ms187540.aspx
Also have you tried increasing your retry configuration parameters to handle the larger mail queue that you are sending through?
Jonathan Kehayias | Senior Consultant,
SQLSkills.com
SQL Server MVP | Microsoft Certified Master: SQL Server 2008
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Please click the Mark as Answer button if a post solves your problem!

Sent E-mails Not Saved In Sent Folder

A while back I posted a topic about randomly sent e-mails not being saved in the Apple Mail Sent folder. At the time I thought it had something to do with AOL. BTW, I am using Apple Mail to access AOL's e-mail servers.
I am also using Apple Mail to access the e-mail servers for a web account I have with Your-Site.com. The same thing happened. I was sending an e-mail with a 6MB attachment. The Apple Mail status bar was holding steady at the half way mark. But it was not moving for about 2-3 minutes. Eventually the status bar disappeared. I checked my Sent folder and the e-mail I sent was not listed. No error messages. I did happen to bbc myself to another e-mail account that I have and it did make it there. But I have no idea if the e-mail was received by the company who I addressed it to.
I sent a follow-up e-mail to ask if they have received it but have not heard anything back.
Should I assume they got it since the bbc was successful?
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I have the same problem, and I think my mail is an older version 1.3.11 (I don't know why it's not updated though!!) Anyway... it's very frustrating, but I know that even it's not copied in the sent forder, the recipient receive the message. But We don't have any proof until the recipient reply or tell us that he had it. I could say that 97% of my message are copied in the sent folder and the other 3% is lost I don't know where... Why ? I don't understand... I there a probleme with the server .mac or the Mail app. ???
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Yahoo sent mail not saved to server when using Mail only.

Why does my Yahoo sent mail not get saved to the server when I use Apple's Mail program? (I have it saved in settings to keep sent mail on server). I can see it in my Sent mail folder on Apple Mail but not on the yahoo server. It's an IMAP account and it works fine on my iPhone.
I have tried changing the outgoing ports as well and erasing the account and reinstating it on the Mail program. No luck.

NatMac:
This worked for me:
ernestobenedict London
This solved my questionRe: Yahoo Mail folder behaviour with Apple Mail 5.0
Dec 8, 2011 5:14 PM (in response to ernestobenedict)
I finally figured out how to fix this; under the mailbox menu there is an option to "use this mailbox for" that allowed me to select the Sent Items folder from my Yahoo IMAP list of folders and make it the default for sent items from the Mac OS X mail software! "
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Yosemite Mail mail not saving preferences

OS X 10.10, Mail 8.0
I have several mail accounts set up, a mix of POP and IMAP
One IMAP account does not use secure authentication.
If I set the preferences for the account under the Advanced tab, and tick 'Allow insecure authentication', then save preferences, I can send mail to the account.
However if I return to Mail after 5 minutes or so the preference has changed back to disallow insecure authentication, and that mail account no loner works. I get a message:
"Mail cannot send your password securely to the server. You can remove this restriction in the Accounts preferences by setting “Allow insecure authentication”, which could put your password at risk."
I have a POP account for a different email address with the same provider, and the preference to allow insecure authentication is saved.
I have tried deleting the account and setting it ip again, but the IMAP presence to use insecure authentication is still not saved.

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Mail not saving large outgoing messages

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