Yosemite Mail still has sync problems with Gmail - any solutions?

My biggest problems experienced in Mail.app since the beginning have stemmed around the Mailbox Behaviors tab. I have tried every single combination of settings there and I still can not achieve what I want, especially with draft messages. It's probably just that I don't use Gmail as Google wants me to...I HATE archiving messages. When I delete a message I never want to see it again after the 30-day period it hangs around (which is fine). For most users this is contrary to their usage, as they want to keep all their old messages.

If you search for the best way to configure the settings in Mailbox Behaviors, you'll find absolutely no consistency of advice, and I certainly don't want to configure them as Google wants (because they want me to archive). One of the things that happens to me in Mail.app is often I'll see about 50 copies of the same draft, but the biggest problem is that drafts will not disappear after I send the message. This latter issue drives me crazy...when I send a message, why does Mail.app keep the draft?

Larry,

Yes, I agree that the plethora of contradictory advice about Mail settings on the web has been very frustrating.

All I can do is share what's working for me. I have three accounts, all hosted by Gmail (one is a regular Gmail account, the other two are employment-related and supported by "Google Apps"), and all are configured nearly identically. Not the "Outgoing Mail Server" comment below which can trip you up if not set properly when one has multiple Gmail accounts.

1. Under the Preferences > Accounts tab:
   • Mailbox Behaviors: All boxes are checked EXCEPT the "Store draft messages on the server", which is unchecked. All three pull-down menus are set to "Never".
   • Account Information:
     • Account Type: IMAP
     • Description: (A name that you choose)
     • Alias: (My return address, if different than official Gmail address)
     • Email address: Same as Alias
     • Full Name: Your name as you want it on outgoing messages
     • Incoming mail server: imap.gmail.com
     • User Name: Same as e-mail address
     • Outgoing Mail Server: IMPORTANT: It is my understanding that each account needs to have a different entry here; do not let two accounts use the same entry. So, when editing the SMTP server list from that menu, create a different entry for each account even though they all use smtp.gmail.com. Description is whatever you want, "Server Name" is smtp.gmail.com, "TLS Certificate" is none. Under the Advanced tab, I have "Automatically detect and maintain account settings" checked, Port 25 (although one of my three accounts uses port 587; don't know why), SSL checked, Authentication "None", "Allow insecure authentication" unchecked.
   • Advanced:
     • Automatically detect and maintain account settings: Checked
     • Include when automatically checking for new messages: Checked
     • Compact mailboxes automatically: Checked
     • Automatically download all attachments: Checked
     • Send large attachments with Mail Drop: Unchecked
     • IMAP Path Prefix: (Blank)
     • Port: 993
     • Use SSL: Checked
     • Authentication: External (TLS client Certificate)
     • Allow insecure authentication: unchecked
     • Use IDLE command if the server supports it: checked
2. Preferences > General: Nothing seems crucial here, although I have "If outgoing server is unavailable" set to "Show a list of alternative servers".
3. Preferences > Junk Mail: I have "Enable junk mail filtering" turned off, since Gmail handles that.
4. I don't see anything else in the other tabs that would make a difference in Mail functioning properly. I can share those settings if helpful.

As I mentioned in my previous post, if you are using an iOS device on a Google Apps account, you need to take the steps that I mentioned for e-mails to be properly deleted vs. archived and to have the proper outgoing address. (I neglected to mention in that post that those steps are for Google Apps-based Gmail accounts, not necessarily regular Gmail accounts, but I can't go back now and edit that message to clarify that point).

I'm currently on travel, but will tweak the settings a bit and try it again when I return home this weekend. A couple of things come to mind, though...first, I agree the mobile iOS settings mentioned by FJ9999...they are correct. This is something that's been known for a long time and I've always been doing them. I suppose you wouldn't have to worry about them if you archived everything instead of deleting. But some things I archive and others I delete...mostly the latter.

Also, it does make sense to me to keep unchecked the "Sent" messages in Mail.app, this has never given me a problem and it ensures that anything I send with Mail.app is displayed in Gmail when I look there.

There have to be other factors, I use Gmail with Mail and without any of these problems. I also use iCloud (which is far better with Mail than Gmail is)

What do you mean you have it checked, checked to do what?

Doug, I'm now on day two with no apparent problems, but I'm still not sure I can keep using Mail.app because of another intolerable issue. Not to hijack this thread as it's already posted elsewhere, but with the inability to turn off swiping it's just too easy to trash a message when using my mouse and my iMac. I understand having swipe gestures for my MBP and there I like them...but it's too problematic with a mouse and can't be turned off.

I agree...there's a lot I like about Mail.app and always have, but sometimes the few things missing from Gmail drive me crazy...UNDO being one of the biggest.

I already knew about changing the left swipe between Archive and Trash (I have it on Trash) but I just dislike it altogether on my iMac or when using a mouse. Like you, it's very helpful on my MBP, which I only use rarely when I travel. Not sure if you knew, but the left swipe feature works in other places as well, such as a Contact, where you can swipe left to delete, but no right swipe is available. It's dangerous here as well as you can easily delete a contact and there is no UNDO (see above).

I'll be interested to see what specific features you like better about Mail.app...maybe you'll also add those you don't like (features, not problems).

There was a time in my (business) life I couldn't do without being able to assign multiple labels to a message. But after retirement, I've started implementing the KIS principle more and more and I really like the idea of having only one folder for one purpose, so for that Mail.app works great for me.

Regarding the UNDO, I'm referring to the Gmail feature you can set to not really send a message for up to 30 seconds. The "UNDO" sits at the top of the UI and you can click it at any time to retract sending a message you may have sent in haste. Mail.app doesn't have this.

The other thing that drives me crazy about Mail.app is I want the message composition window to be where "I" want it...not stuck on the right side of my display where it always display when I create a new message. I know, many users dislike that Gmail puts it in the lower right corner, but at least you can change that to a default larger window in the middle of the UI.