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Mail app keeps resending already sent emails. How do I fix this?

One of my accounts, an IMAP account if it matters, will resend emails sent in the last week or so when Mail app is launched. This is embarrasing, confusing and annoying to the recipients. What can I do to fix this?


Scrolling through the discussions I found a couple of answers:

This problem is caused by some index corruption that makes messages to randomly appear in a mailbox different from where they’re supposed to be. If that mailbox happens to be the Outbox, Mail thinks they’re waiting to be sent and dutifully proceeds to try to send them.

Verify/repair the startup disk (not just permissions), as described here:

The Repair functions of Disk Utility: what's it all about?

After having fixed all filesystem issues, if any, and making sure that there’s enough space available on the startup disk (a few GB, plus the space needed to make a backup copy of the Mail folder), try this:

1. Quit Mail if it’s running.

2. In the Finder, go to ~/Library/Mail/. Make a backup copy of this folder, just in case something goes wrong, e.g. by dragging it to the Desktop while holding the Option (Alt) key down. This is where all your mail is stored.

3. Locate Envelope Index and move it to the Trash. If you see an Envelope Index-journal file there, delete it as well.

4. Open Mail. It will tell you that your mail needs to be “imported”. Click Continue and Mail will proceed to re-create Envelope Index -- Mail says it’s “importing”, but it just re-creates the index if the mailboxes are already in Mail 2.x format.


I tried all this, but when I attempted to relaunch Mail I received an import failed message. I also tried deleting my com.apple.mail.plist file and that didn't work either. I'm still sending already sent messages when Mail app launches.

HELP!!

MacBookPro1,1, Mac OS X (10.4.8)

Posted on Mar 6, 2007 12:18 PM

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Question marked as Best reply

Posted on Mar 6, 2007 1:32 PM

It may certainly matter that the account is IMAP. Try the following variation of the procedure to re-create the index:

1. Quit Mail if it’s running.

2. In the Finder, go to ~/Library/Mail/. Make a backup copy of this folder, just in case something goes wrong, e.g. by dragging it to the Desktop while holding the Option (Alt) key down. This is where all your mail is stored.

3. Locate Envelope Index and move it to the Trash. If you see an Envelope Index-journal file there, delete it as well.

4. Move the “IMAP-” account folder to the Trash. Note that you can do this with IMAP-type accounts because they store mail on the server and Mail can easily re-create them. DON’T trash any “POP-” account folders, as that would cause all mail stored there to be lost.

5. Open Mail. It will tell you that your mail needs to be “imported”. Click Continue and Mail will proceed to re-create Envelope Index -- Mail says it’s “importing”, but it just re-creates the index if the mailboxes are already in Mail 2.x format.

6. As a side effect of having removed the IMAP account folder, that account may be in an “offline” state now. Do Mailbox > Go Online to bring it back online.

Note: For those not familiarized with the ~/ notation, it refers to the user’s home folder, i.e. ~/Library is the Library folder within the user’s home folder.
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Question marked as Best reply

Mar 6, 2007 1:32 PM in response to Trevor Nomi

It may certainly matter that the account is IMAP. Try the following variation of the procedure to re-create the index:

1. Quit Mail if it’s running.

2. In the Finder, go to ~/Library/Mail/. Make a backup copy of this folder, just in case something goes wrong, e.g. by dragging it to the Desktop while holding the Option (Alt) key down. This is where all your mail is stored.

3. Locate Envelope Index and move it to the Trash. If you see an Envelope Index-journal file there, delete it as well.

4. Move the “IMAP-” account folder to the Trash. Note that you can do this with IMAP-type accounts because they store mail on the server and Mail can easily re-create them. DON’T trash any “POP-” account folders, as that would cause all mail stored there to be lost.

5. Open Mail. It will tell you that your mail needs to be “imported”. Click Continue and Mail will proceed to re-create Envelope Index -- Mail says it’s “importing”, but it just re-creates the index if the mailboxes are already in Mail 2.x format.

6. As a side effect of having removed the IMAP account folder, that account may be in an “offline” state now. Do Mailbox > Go Online to bring it back online.

Note: For those not familiarized with the ~/ notation, it refers to the user’s home folder, i.e. ~/Library is the Library folder within the user’s home folder.

Mar 6, 2007 1:40 PM in response to David Gimeno Gost

When I try the variation proposed I still get a message saying, "The import failed." The entire message is:

An error occurred during the import. Please make sure you have plenty of available space in your home folder and try again.

fyi: I have 20GB of free disk space.

Additionally, it may or may not be related, I keep getting a seperate message saying, "Your Mac OS X startup disk has no more space available for application memory. To avoid problems with your computer, quit any applications you are not using." I mention this problem because it appears when I try and launch Mail...

Mar 6, 2007 1:54 PM in response to David Gimeno Gost

I really did use Disk Utility to repair permissions:

Repairing permissions for “Macintosh HD”
Determining correct file permissions.

Permissions repair complete
The privileges have been verified or repaired on the selected volume


Only one partition as well:

Intel ICH7-M AHCI:

Vendor: Intel
Product: ICH7-M AHCI
Speed: 1.5 Gigabit
Description: AHCI Version 1.10 Supported

ST9100824AS:

Capacity: 93.16 GB
Model: ST9100824AS
Revision: 7.01
Serial Number: 5PL0XQ0E
Native Command Queuing: Yes
Queue Depth: 32
Removable Media: No
Detachable Drive: No
BSD Name: disk0
OS9 Drivers: No
S.M.A.R.T. status: Verified
Volumes:
Macintosh HD:
Capacity: 92.84 GB
Available: 19.07 GB
Writable: Yes
File System: Journaled HFS+
BSD Name: disk0s2
Mount Point: /

Mar 14, 2007 6:47 PM in response to David Gimeno Gost

So I attempted to repair my disk by booting from the Installation DVD. I ran Disk Utility and received this error while trying to repair the disk.

First Aid Failed

Disk Utility stopped repairing "disk" because the following error was encountered.

The underlying task reported failure on exit.

Now what? Sounds like the hard drive is toast...

Mar 14, 2007 7:19 PM in response to Trevor Nomi

If Disk Utility reports problems it cannot fix, even when starting up from a different disk, you’ll need a more powerful disk utility, such as DiskWarrior, TechTool Pro, or Drive Genius.

The “Disk Utility cannot repair the disk” section of the following article has some additional information you may also find useful:

Resolving Disk, Permission, and Cache Corruption

Mail app keeps resending already sent emails. How do I fix this?

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