Mail resends old mails on its own

Greetings, I am following this with interest. Recently my iBook (10.4.2) Mail began this behavior (but not the iMAc 10.3.5 that uses the same POP mail account). I am in slight dread of the telltale whoosh. Thoughts, probably irrelevant -- (1) The behavior began after I recently did a bunch of software updates including security updates 2005-007 and 008 and others. (2)I'm checking with the ISP about a detail about authentication.

I'm having the exact problem. My IMAP mail is on an Xserve and I have a G4 tower with an Apple wired keyboard and a mighty mouse. I have another Tiger user that is having this problem as well. It has to be Mail app related.

I checked with my ISP. My ISP email is POP with webmail, that is, while I normally work with Mail and download to, or send messages from, my machine, unread copies sit in the webmail for a week or so. When traveling, I can work with the webmail directly. Anyway, the ISP support thinks the occasional re-send is caused, in some manner, when there are many unread or sent messages in the webmail and Mail has difficulty handling all of them when it first connects and starts processing. He also implies the problem can be seen in some other mail apps. Strangely, it is true that the re-sending started after a trip when I sent mail to home using the webmail. 2 weeks later I haven't had a re-send lately.

Oh, sorry, prior note didn't include the ISP's suggested solution: delete most messages from the webmail.

I'm having the same problem. The affected computer is a 600 MHz iBook with no external keyboard or mouse. The problem has occurred before and after an upgrade to 10.4.3. My e-mail comes from a POP3 server, where the mail resides for a time. The problem affects both received mail and sent mail. The behavior almost always occurs on initial launch of Mail or on waking from sleep when Mail is running.

The problem has two manifestations:
1) A whoosh and a quick, temporary switch of the mailbox "Sent" to "Sending".
2) The appearance of an "Outbox" in the mailbox list. When this happens, a count will appear. If I click on "Outbox", I see one message. If I delete that message, the duplicate message will also disappear from wherever it was (Inbox, Sent, or Trash). If I then switch the the Inbox and back to Outbox, a different message will appear on the Outbox.

I doubt that this problem involves messages being kept on the POP3 server, as it also affects send mail.

William,

This is a very puzzling report. In the Finder, open Home/Library/Mail and report the files and folders at the first level -- disguise account folder names to not reveal your email addresses.

Furthermore, open the Mailboxes folder, and report that the Outbox.mbox folder is to found there. Also, in at least one of your POP accounts where this happens, open the INBOX.mbox folder, and report each file and folder within.

More info, please.

Here's the information that you requested. To explain, almost all my e-mail comes through a prior ISP. I only use my current ISP to provide an SMTP server and my DSL connection.

~/Library/Mail:
MessageRules.plist
Mailboxes
LSMMap2
Envelope Index
DefaultCounts
Signatures
POP-bsboyd@pop.<myisp>
POP-bboydcssf@pop.<prior-isp>
OpenedAttachments.plist
MessageSorting.plist.backup
MessageSorting.plist
MessageRules.plist.backup
SmartMailboxes.plist

~/Library/Mail/Mailboxes:
TidBITs.mbox
<ISP>.mbox
Outbox.mbox
Saved E-mail
Registrations.mbox
Transactions.mbox
Junk.mbox
Saved E-mail.mbox
Deleted Messages.mbox
<prior-ISP> Saved Mail.mbox
Loan Messages.mbox

~/Library/Mail/POP-bboydcssf@pop.<prior-isp>.com:
Sent Messages.mbox
Drafts.mbox
MessageUidsAlreadyDownloaded2
Deleted Messages.mbox
INBOX.mbox
MessageUidsAlreadyDownloaded

William,

Open the folder INBOX.mbox from the prior isp account folder (in the Finder, again), and report the files and folders within.

Although I think the Outbox.mbox may somehow be corrupt, I have not seen any form result in this situation, so there may be more at work. Nevertheless, quit Mail, and delete the Outbox.mbox folder from the Mailboxes folder. Relaunch Mail, and compose and send a message -- Mail will create a new Outbox.mbox. Test to see if this alone resolves. However, I am also concerned that files leftover from earlier versions of Mail may still be present in your xxxx.mbox folder -- thus the question about the contents of the INBOX.mbox.

More info, please.

Here's the contents of ~/Library/Mail/POP-bboydcssf@<prior-isp>:

mbox
Messages
content_index
Info.plist
table ofcontents

There are messages in that Inbox that date to May 2004. Is that ill-advised?

I deleted Outbox.mbox from ~/Library/Mail/Mailboxes. I also deleted from that an empty folder named "Saved E-mail" (There's also a folder named "Saved E-mail.mbox", which I kept.) When I relaunched Mail, it promptly sent a message. (At least, "Sent" changed to "Sending..." and a "whoosh" sound occurred. I couldn't find any other evidence that a message had been sent.)

I have some additional observations about my problem. I turned off my computer's connection to the Internet so that messages would persist in the Outbox. When I launched Mail, the Outbox appeared with one message in it. I opened the message and was able to identify the folder containing the original message, which was still there. When I tried to drag the Outbox message to another folder, that folder would hightlight (indicating acceptance) unless I tried to drag the message to the original folder of the message.

Does this suggest that the message in Outbox and the message in the original folder are actually the same message? Or is Mail just rejecting an attempt to put two messages with identical subject, date/time, etc. in the same mailbox folder?

William,

Have you set up any Smart Mailboxes? If so, where?

What you have reported about the contents of the INBOX.mbox for your account with prior ISP, is consistent with what I was saying about leftover files. See:

http://docs.info.apple.com/article.html?artnum=301315

All xxxx.mbox folders should be cleaned up have ONLY a file named Info.plist, and a folder named Messages -- the latter contains the actual message content, and has a file for each message. All the others should have last date modified info consistent with when you upgraded.

However, I have not seen the leftover files cause the specific situation you have with Mail being sent, repeatedly, upon startup.

Let me know when you have completed the cleanup of all your xxxx.mbox folders, and also about whether you have used Smart Mailboxes anywhere.

Ernie

No smart mailboxes.

I did all the cleanup. I still have the problem.

I just watched Mail cycle through messages. It went down the list of one mailbox, then proceeded to each mailbox down the list.

I also did an experiment to clarify the issue of moving the Outbox messages. I selected a message in the Inbox and used menu item "Message -> Copy to" to create a copy of the mesage in another folder. I discovered that I could move the new message back into the original folder. This suggests that the messages in Outbox, which Mail doesn't allow me to move into the original folder, is actually the same message as the original, not just a copy. If that's true, then Mail seems to be scrambling the message list.

I finally solved my Mail sending problem by brute-force rebuilding of the Mail contents in ~/Library. First I moved all e-mail from account-oriented folders (Inbox, Sent, and Trash) into folders that were not account-specific. Then I quit Mail and moved ~/Library/Mail to the Desktop. I launched Mail, entered my account information, defined the same set of local mail folders that I had before, visited each local folder, and changed the sort order to cause Mail to create an Info.plist file. I then quit Mail again and moved the Messages folders from each mailbox folder of the saved Mail folder to the corresponding folder in ~/Library/Mail/Mailboxes. I launched Mail once more, then visited each local folder and invoked Mailbox -> Rebuild.

I could probably have skipped some of those steps, for example, by moving the saved local folders directly to ~/Library/Mail/Mailboxes instead of defining them in Mail.