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Having problems setting up GMail to work seamlessly with Apple OS X Mail? I was. It was the bane of my existence for awhile and continued getting worse until I’d had enough. Having multiple e-mail accounts spread across multiple computers (and devices) I’m sure didn’t help, but I’m sure a lot of you out there have the same issue, so hopefully this will make your life a little less difficult.

I have to admit, I set up GMail to work with POP mail a long time ago, then switched over to a .mac IMAP account and relegated GMail’s POP-only solution to the backseat. Nothing in the world beats IMAP (at least when it’s set up and working properly), not having to worry about marking messages as read when moving to a different computer, or devoting a couple of hours every month to clean-up, trying to get everything in sync, or wondering which hard drive had that crucial message I needed to refer to at any particular moment. Frankly, deleting a batch of messages on my iPod Touch while I’m waiting for a bus, then having that reflected on the e-mail client on my main computer is downright elegant. It’s the way everything should work.

Okay, so my first issue when I finally started setting up IMAP GMail accounts in Apple Mail (Google added IMAP support to GMail around the end of October last year) was that they weren’t quite so elegantly transparent as the .mac solution, which, to be fair, was created with Apple Mail in mind. This is mainly because GMail uses different folder name than .mac or Apple Mail, specifically, “Sent Mail” vs “Sent” and “Spam” vs. “Junk”, so GMail creates its own set of folders for the folders that you already have set up in your “On My Mac” mail. What this means is when you get a new bit of Spam to your GMail account (something I get a lot of) it goes into the “Spam” folder in GMail because GMail applies its own rules (which you can’t turn off) separate from Apple Mail’s own “Junk” rules. So you end up managing two (or more) folders for junk, and pretty much end up actually looking at the messages you aren’t supposed to be bothered with as you flag them again and again as junk in Apple Mail.

I honestly didn’t think there was a solution for this until I started dgging around yesterday, and it turns out Apple has made it incredibly simple.

Anyway, step-by-step, just go ahead and set up your GMail account in Apple Mail following the instructions Google provides, which can be found here. Immediately following this, you’re going to want to make one change: under Accounts, click on your GMail account, then go to the “Advanced” tab. Here, under “IMAP Path Prefix”, type “[Gmail]” (without the quotes). Then click on another tab and choose “Save” when prompted. This gets rid of the extra folder name, [Gmail], in the sidebar. Seems like a small point, but one less folder to have to worry about, the better.

Next, in your main mailbox, the exciting point that I was hinting at above that will make your life a hell of a lot easier … expand your new GMail hierarchy in the sidebar. You should see “All Mail”, “Drafts”, “Spam” etc. Click on “Drafts”, then from the main menu, choose “Mailbox” + “Use This Mailbox For” + “Drafts”. Then do the same for “Sent Mail”, “Spam” and “Trash” (choosing the appropriate option for each, or course).

Voila! After some chugging away, talking back and forth with the server, all your GMail Sent Mail, Drafts, Junk and Trash should now go to the appropriate pretty icons in Apple Mail. This made an absolutely huge difference for me and I couldn’t believe it was such an easy fix considering how long I’d been suffering through extra folders.

So, yeah, I was happy. For awhile. Then the problems started. I found that after using this set up for only a few minutes, that suddenly all my GMail accounts stopped communicating with the server. I just kept getting the timed out while trying to communicate with port 993 error. Maybe it was because I had multiple accounts, maybe it was because I had mixed accounts. Who knows. Anyway, it turned out that the fix was a particularly goofy one. Basically, I just set the passwords for each of the accounts to something they weren’t (like “sdgdsdf”), then saved my settings. Immediately, Apple Mail prompted me for passwords for each, which I entered correctly (choosing “Save to keychain”) and what do you know, I’ve been running nearly 24 hours error free. GMail problem? Leopard problem? Who knows. It works though.

Now, the only lingering thing that bothers me are the main GMail folder dregs that are sitting in my sidebar (”All Messages” and “Starred Messages”). If anyone knows how to wipe these out, please leave a comment below, I’d appreciate it. I hate having stuff sitting around that I will never click on.

I have yet to try syncing the newly re-set up accounts with .mac or iPod. When I’d initially set up a second computer some time ago, using the “sync mailboxes” feature of .mac, I got screwed-up accounts on the second computer. On my iPod Touch, I’ve got duplicates for all my accounts. So I guess this is the next thing I have to look at (apart from Font Book issues, which will probably be the topic of the next post).

Hope you found this helpful.

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