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

Anonymous

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.

Locked Question. This question was migrated from the Microsoft Support Community. You can vote on whether it's helpful, but you can't add comments or replies or follow the question.

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Anonymous

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

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

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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51 additional answers

Anonymous

2012-05-18T04:35:37+00:00

Regarding renaming a folder...Put Outlook into Work Offline. Rename. Select Work online and it should stick.

In Outlook SP2, you should not be connecting to Gmail's All Mail folder.

When you move a message from a folder it's archived in All Mail. This is specific Gmail behavior.

Gmail handles deleting vs trashing differently. Delete removes it from the folder buy not the All mail folder. Trashing really deletes it.

GMAIL'S RECOMMENDED IMAP CLIENT SETTINGS

Sending:

Do NOT save sent messages on the server. If your client is sending mail

through Gmail's SMTP2 server, your sent messages will be automatically

copied to the [Gmail]/Sent Mail folder.

DO save draft messages on the server. If you want your drafts in your mail

client to sync correctly with Gmail's web interface, set your client to save

drafts to the [Gmail]/Drafts folder.

Deleting:

Do NOT save deleted messages on the server. Messages that are deleted from

an IMAP folder (except for those in [Gmail]/Spam or [Gmail]/Trash) only have

that label removed and still exist in All Mail. Hence, your client doesn't

need to store an extra copy of a deleted message.

Do NOT save deleted messages to your [Gmail]/Trash folder because this will

delete a message in all folders.

Do NOT save deleted messages to your [Gmail]/All Mail folder as some clients

will try to empty this folder and ultimately fail. This can lead to delayed

mail access or excessive battery consumption on a mobile device.

Junk mail and spam:

Do NOT enable your client's junk mail filters. Gmail's spam filters also

work in your IMAP client, and we recommend turning off any additional

anti-spam or junk mail filters within your client. Your client's filter will

attempt to download and classify all of your existing messages, which may

slow down your client until the process is complete.
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Anonymous

2012-05-18T04:25:27+00:00

Even though I knew this was unrelated to the issue I was experiencing, I went through the procedures in this KB article, to no avail.

I have 42 years experience in the computer industry, including in support roles and system administration on a large campus. I have a reasonably good understanding of how IMAP works and also how Gmail's implementation of IMAP maps to its own Labels system, together with its limitations and gotchas.

This problem is specific to to Outlook 2011 (probably only to the 14.2.x versions) and as part of investigating this problem I am continually comparing behaviour of Outlook 2011 versus Entourage 2004, Entourage 2008 and IOS Mail, across several different accounts.

Gmail is usually pretty good at detecting and eliminating duplicate emails (I have been pleasantly surprised to see it doing this successfully on imports of large (tens of thousands) imports of emails from other mail archives), but something is going on here with the way Outlook 2011 handles moving messages between folders.

I am fairly sure this problem did not occur with the 14.1.x versions (I can see no evidence of it in the All Mail folder) but I am not about to attempt a second rollback to 14.1.4 (I already had to do this once after the 14.2.0 update created chaos with tens of thousands of existing messages across several accounts) - I was not the only one to experience that problem and the resulting clean-up job.

Dave
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