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A friend has two iMacs (10.6.5), iPad & iPhone (iOS 4.2) recently switched to gmail for his primary email service.

The problem is that not all the devices see the same Sent, Drafts and Trash mailbox.

Working with other IMAP services, I never see issues like this, so I know this is a gmail specific issue - theres a disconnect between the way Gmail organizes its IMAP mailboxes vs. the way the Apple Mail does.

For instance, when you configure Apple Mail for a gmail IMAP account, it assumes your Sent mailbox will be called Sent Messages. And on the gmail web side, a Label always gets created called Sent Messages. My experience is that without any intervention, when you send email, it shows up in Apple Mail in the proper Sent mailbox, but in gmail it shows up in Sent Messages, NOT gmails Sent mailbox.

For some reason, with a gmail account, the old trick of Mailboxes > Use this Mailbox for doesnt work because the options are grayed out.

So, how Ive improved this situation is to open up PropertyListEditor and edit com.apple.mail.plist. There is a key called MailAccounts under which is an item representing the Gmail account. Underneath, theres an entry for SentMessagesMailboxName. Ive tried changing this to both Sent Mail or [Gmail]/Sent Mail and both work in the sense that any email sent from Apple Mail ends up in gmails Sent mailbox, and NOT in Sent Messages

So far so good, but heres where the mystery deepens.

In my friends situation (and a couple other Macs I've worked on ), when I do this, when path is set to [Gmail]/Sent Mail, I see two Sent mailboxes
* * * * in Apple Mail, I see 886 messages in the Sent under Mailboxes, and 823 in Sent Mail under GMAIL section
* * * * in gmail, the Sent Mail mailbox has 651 items and there exists a [Imap]/Sent Mail mailbox which has 609 items
When I edit the plist and change the path with PropertyListEditor to just Sent Mail, Apple Mail only shows one Sent mailbox with 823 messages items, but is missing the message sent within the past couple days.

Any ideas how to make sense of this? What is the best way to setup the Apple Mail preferences?