Moving a message to another mailbox (or Gmail's Trash) generates a second duplicate copy of the message in All Mail

Anonymous
2012-05-17T02:40:58+00:00

Original title: Gmail IMAP issues with Outlook 14.2.2

Outlook 14.2.2 is still not playing ball well with Gmail IMAP.

Moving a message to another mailbox (or Gmail's Trash) generates a second spurious copy of the message in All Mail. Each subsequent move of the message creates yet another spurious copy.

It also will not let me rename a Gmail IMAP folder. After selecting 'Rename Folder', the normal highlighted text box shows but reverts before you have time to make changes.

Selecting a mailbox and pressing Command-Delete moves the whole mailbox and its messages to what looks like the Gmail Trash, but is not regarded as being within Trash by Gmail, which treats it as a separate Label.

(Account/Advanced/Folders/Trash is set to point to Gmail's Trash mailbox. Actually 'Bin' in our localised version.) Works fine with other mail clients.

These problems do not occur with Exchange Accounts.

Outlook | MacOS | Legacy Outlook for Mac | For business

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Anonymous
2012-05-21T10:38:43+00:00

Dave's Recommended Settings for Best Gmail-Outlook (2011) Compatibility

Gmail:

Go to Gmail on the web.

Under Settings > Forwarding and POP/IMAP > IMAP Access:

  • Status: Enable IMAP
  • When I mark a message in IMAP as deleted: Auto-Expunge off - Wait for the client to update the server.
  • **When a message is marked as deleted and expunged from the last visible IMAP folder:**Move the message to the Bin
  • Folder Size Limits: Do not limit the number of messages in an IMAP folder (default)
  • I aso recommend that you disable****POP Download, as allowing a default configured POP email client to access your Gmail account could result in loss of messages form your IMAP client.
  • Save Changes.

Under Settings > Labels:

Uncheck Show in IMAP for the following labels:

  • Starred
  • Important
  • Chats
  • All Mail

Outlook 2011:

Under Outlook Preferences > Accounts > (your Gmail account) > Advanced > Folders:

  • Store sent messages in this folder: Choose (your Gmail account) > [Gmail] > Sent Mail
  • OK and close Outlook Preferences completely. I will explain the reason for this seemingly odd step later. *
  • Re-enter Outlook Preferences > Accounts > (your Gmail account) > Advanced > Folders and continue settings as below:
  • Don't store a copy of sent messages (but the greyed out drop-down must still show "Sent Mail (Server)"
  • Store draft messages in this folder: Choose (your Gmail account) > [Gmail] > Drafts
  • Store junk messages in this folder: Choose (your Gmail account) > [Gmail] > Spam
  • Move deleted messages to this folder: Choose (your Gmail account) > [Gmail] > Trash (or Bin if your local language settings show as this)
  • When Outlook closes, permanently erase deleted messages: Never. (The result of this setting is that Gmail will automatically delete messages after 30 days anyway. If you prefer, you could set a shorter interval here.)
  • OK and close Outlook Preferences completely.

Under Tools > Junk E-mail Protection... > Level:

  • None: Turn junk e-mail protection off. (This allows Gmail's very good Spam protection to manage your junk e-mail. Providing you have also made the settings in the section above, you can use the Junk ribbon item in the Home tab to send or remove messages to or from Gmail's Spam folder. However, it will have the side effect of disabling junk protection for any other accounts you may have configured in Outlook.)
  • OK

* Why the seemingly odd step of setting and then unsetting the "**copy of sent messages"**setting?****If you do not do this, and you have Outlook Preferences > General > Folder List > Group similar folders... checked, the Sent Items > (your Gmail account) in the Navigation Pane will appear empty and you will not see your Sent Mail in this folder.

With these settings, Outlook 2011 14.2.2 will play well with Gmail IMAP.

Dave.

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Anonymous
2012-05-21T10:15:55+00:00

I have done further research on this problem and have come up with a workaround. This involves changing a setting in Gmail's IMAP configuration.

The Workaround:

Go to Gmail on the web. Under Settings > Forwarding and POP/IMAP > IMAP Access.

  • Change "When I mark a message in IMAP as deleted:" to "Auto-Expunge off - Wait for the client to update the server."
  • Change "When a message is marked as deleted and expunged from the last visible IMAP folder:" to "Move the message to the Bin"
  • Save Changes.

The effect of this change is that:

  • Deleting a message in Outlook 2011 14.2.2 will move the message to Gmail's Trash folder.
  • Moving a message in Outlook 2011 14.2.2 will move the message to the selected target folder.
  • Either of the operations above will generate a spurious duplicate of the message, but that spurious duplicate will be filed in Gmail's Trash and eventually be deleted after 30 days. Without this change, the spurious copy is filed in "All Mail" and stays there forever (wasting quota and also a security issue for apparently deleted emails).

In order to check whether this Gmail setting change caused any adverse effects with other IMAP clients, I tested the Delete and Move behaviour (after the Gmail setting change) on the following clients:

  • Entourage Mac 2004
  • Entourage Mac 2008
  • Outlook Windows 2010
  • IOS (iPad) Mail

In all cases, these mail clients continued to function correctly for Delete and Move operations and did not generate spurious duplicates.

I concluded that this workaround gives the best results with Outlook 2011 14.2.2 without adversely affecting the other IMAP mail clients I tested.

In a separate post, I will enumerate in full the settings (both Gmail and Outlook 2011) that I have found give maximum compatibility between Gmail & Outlook 2011.

Dave

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Anonymous
2012-07-26T16:10:09+00:00

Once I found out that I had to remove Outlook (client) rules and rely on Gmail filters to do the rules behind the scenes (on the server), then duplicates stopped.  Thanks Dave and Scott!

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  1. Anonymous
    2012-05-18T18:51:59+00:00

    The product team at Microsoft is aware of the duplicating Gmail mail when moving messages between folders issue.

    I find that using smart folders rather than rules to view Gmail messages works better than using rules. In addition using Filters in Gmail to move before download helps too.

    I'm sorry if you felt like I was regurgitating the basics, but other users that search for answers might not know these so I try to include info for all levels of users.

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  2. Anonymous
    2012-05-18T09:24:22+00:00

    Sorry, regurgitating GMAIL'S RECOMMENDED IMAP CLIENT SETTINGS from the Google help page is of no benefit. I know that page very well. I am looking at several real issues, which are being handled incorrectly by Outlook 2011 and no other email client I have tested.

    I know exactly how Gmail handles deleting and Trashing and how that relates to the All Mail  folder. You may care to read <http://support.google.com/mail/bin/answer.py?hl=en&answer=77657>How do actions sync in IMAP? which will explain it better.

    And, no I am not connecting  to Gmail's All Mail folder in an IMAP client. I'm not that stupid. I am viewing the All Mail folder in Gmail web interface to check if Outlook is doing what it is told to do by my configuration.

    If I set 'Mark messages as deleted', an IMAP client should effectively remove the label and the message will still exist in All Mail. If I set 'Move deleted messages to folder [Gmail]/Trash, an IMAP client should move the message to [Gmail]/Trash and no copy should exist in All Mail.

    LIkewise if I ask an IMAP client to move a message from any folder to another folder, an IMAP client should effectively remove the original label and add the new label to the message. Only one copy should exist in All Mail, and it should carry the new label.

    Entourage 2004, Entourage 2008, IOS Mail and Outlook 2010 (PC) all manage to do this correctly.

    Only Outlook 2011 manages to stuff it up. In the case Move to Trash, it moves the message to [Gmail]/Trash AND leaves a second persistent copy in All Mail. In the case of move between any two other folders, it assigns the message label to the new folder AND creates an extra unlabelled copy in All Mail. If you move the same message to another folder 20 times you will end up with 21 copies of the message in All Mail, one labelled with the last folder it was moved to, the other 20 duplicates unlabelled.

    As far as needing to go Offline to rename an IMAP folder, that is a bug, not correct behaviour. No other email client I have tested needs to be put Offline to rename a folder.

    I always test software thoroughly before rolling it out. I need to in the work I do, and in this case Outlook 2011 SP2 fails the test miserably for Gmail IMAP accounts.

    Dave.

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