How To Wrangle Outlook 2011 To Work With Gmail

As I crane my head back to sigh out a breath of relief, an hour of frustration in Microsoft Outlook 2011 has ended in fist pumping victory. It took blood, sweat, tears, and a chocolate chip cookie, but I’ve jumped into the line of fire so that Gmail (which honestly doesn’t play nice with any desktop mail client) could commingle with Microsoft’s de facto business solution. Microsoft’s default setup is ugly, and I’m here to fix what the Mactopian team wasn’t kind enough to fix for you. So here’s the scoop: As of November 23rd, 2010, this is an accurate guide on how to fit Gmail (the square peg) into Outlook (a round hole). Students with academic licenses and business persons pimping the full suite, click past below for the unadulterated guide of champions.

I don’t know what could have possibly led you to this, but for some reason, Apple’s Mail just isn’t good enough. Despite whatever traumatizing childhood event led to this email crushing decision, at least you’ve got a shoulder to rely on. Without me, you’d be diving head first into a whirlpool of shark infested labels where Outlook devastates your Gmail workflow. If have a bit of patience and fifteen minutes, we’ll morph Outlook into a Gmail rockin’ desktop client fit for the Microsoft guru in you.

Preparing For Outlook: IMAP & Gmail Labs

Before you even dare to open Microsoft Outlook, let’s think about what protocols you want to use with Outlook. By default, Gmail will have POP enabled. If you know what’s good for you, you’ll disable the little twerp and enable the neighborhood king, IMAP. What’s the difference you ask? Without getting into elaborate details, think of POP as a one a way steam train while IMAP is a highly advanced two-way teleportation machine. Anything you do on your computer will be mirrored to Gmail and vice-versa (your content stays on the server), ensuring you’ll always have access to those precious break-up emails no matter where you decide to access your content. You’ll also avoid two of Outlook’s annoyances:

1. POP emails are dumped into Outlook’s My Computer folders (with no regard from which account the POP email came from) which are a pain to deal with.
2. You won’t have to create separate Inbox, Sent, Draft, etc. folders for your Gmail account.

Log in to Gmail and click on the Settings link in the top right corner. If you click on the Forwarding and POP/IMAP tab, you’ll want to select the radio buttons for disabling POP and enabling IMAP. After saving your changes you should end up with something similar to the screenshot below.

We’re not done just yet. Most likely you’re a semi-pro who’s taken advantage of Gmail’s labels. In our initial sync (and to avoid complication), you’ll want to disable syncing them. They’ll show up as folders in Outlook, and we’ll deal with them later. For now, navigate to Labs and enable the Advanced IMAP Controls feature. Upon saving your changes, navigate to Labels, scroll down to the Labels section, and uncheck all the Show in IMAP boxes in this section. If you have no labels, then you have nothing to worry about. Remember, don’t touch the System Labels in the top section unless you want to hide your Priority Inbox and Chats (recommended).

Where We Add Our Gmail Account To Outlook

It’s time to light Gmail on fire  – we’re ready to add it to Outlook.

As a quick interlude, if you’re not already using the My Computer folders, you can disable them by visiting the General pane in the Preferences.

In Outlook, access your Preferences, click Accounts, and add an email account. This will be obvious if Outlook is naked, otherwise you can use the + at the bottom of the accounts panel to add a new email account. If you’re using a Gmail account, Outlook should gobble up your account info and set everything up automatically port wise. However, Google Apps users or those proactive enough to set everything manually will want to follow Google’s word of advice here: http://mail.google.com/support/bin/answer.py?answer=78799

The screenshot below gives you a quick visual rundown of everything you’ll need to set.

Click the Add Account button, and Outlook will aggressively molest Gmail into its architecture.

How Outlook Completely Mishandles Gmail

This is one of those forehead slapping things that I can’t forgive Microsoft for. Outlook is incredibly clumsy in that it’s simply stupid: it doesn’t know how to talk to your Gmail account. Outlook creates four new labels to cope, and in the process completely confuses users who expect the process to just work. Unlike Apple Mail (which is smarter about the account creation process and allows you to Use This Mailbox For…), Outlook forces its own hierarchy into Gmail folders, which are represented as labels. Even though Outlook allows you to change which folders you want to store your messages in, the end result still ends up being incredibly messy since messages end up in the [Gmail] sub-folder and never in your main Drafts, Sent, Deleted, and Junk folders beneath your Inbox. You can see in the screenshot above that you’ll have two sent folders, two trash folders, etc.

Outlook’s and Gmail’s naming conventions are different, and that creates lots of hair pulling conflicts. Here’s how Outlook and Gmail mailboxes compare:

Inbox = Inbox
Drafts (Oddly shows up as [IMAP]/Drafts in Gmail labels) = Drafts
Sent Items = Sent Mail
Deleted Items = Trash
Junk E-Mail = Spam

Outlook’s conventions will show up as Gmail labels, so if you revisit your label settings, you’ll see four new checked entries. While Outlook had good intentions of storing your mail in the server, it should be smart enough to abide by Gmail’s naming conventions. It’s not.

Before you get all willy-nilly and delete the varmints (who wouldn’t?), let’s avoid having Outlook whine about missing IMAP folders and instead rebuild our Gmail account with some advanced settings. Deleting comes later.

Wrangling Outlook & Making Gmail Awesome

Head back into Accounts in the Preferences, and highlight your account in the left pane. Below all of your server details, you should see a More Options button. Click it, and select Use Incoming Server Info from the pull down menu.

Click OK, then click on the Advanced button. Under Server, Check Use IMAP IDLE and clear Stay connected to inbox only (optional). Next comes the part where we fix almost everything Outlook screwed up. In the IMAP Root Folder text box, type [Gmail]. Pigs can fly people.

That’s it. Click OK, exit out of the account preferences, and watch Gmail rebuild itself into a pretty bundle of joy. If all goes well, you’ll see an incredibly less cluttered interface and no more duplicate folders. There is a chance you’ll still have both a Junk E-Mail and Spam folder. In this case, return to your Advanced settings, and under Folders, point Junk to the Spam folder via the pull down menu.

Your labels will be missing (which we’ll re-add in a second), but everything should now be under control. Because your labels aren’t showing up in Outlook, you can remove the four stray labels Outlook added earlier to Gmail.

Even with those “bad” labels removed, how do we add your previous hidden labels back to Outlook? Simple. Enable all of your labels so they’ll Show in IMAP, and rename them by adding a [Gmail]/ prefix. If you exit Outlook and reopen the application your labels will sync effortlessly.

Advanced: Nested [Gmail] Labels, Archiving Instead Of Deleting, And Why Is Everything So Unread?

Let’s say you’re not a big fan of having [Gmail]/ in front of every label under the sun. Visually it’s irritating, but I’ve found a way to make it less so. Entering your labels will still be annoying, but on the bright side, everything won’t look the same.

Remember our Gmail labs feature? Head back to that and enable something called Nested Labels. To use it, create a parent folder like [Gmail]/. To create subfolders, create a new label called [Gmail]/Subfolder for example. The cool thing is you’ll only see Subfolder and not what’s before it. This won’t dramatically effect how Outlook sees things, but it’ll make your organization in Gmail much better since desktop clients throw you for a loop. Trust me, it’s much better seeing one annoying [Gmail] label than a dozen of them in some weird code text, and Mac users savvy enough can probably create a CSS style that’d remove the bugger and scoot the subfolders back over to the left margin.

This doesn’t solve our other annoyances though. Back in Outlook, there isn’t a tremendously easy way to archive data instead of deleting it. If you want to send information to All Mail instead of the Trash, you could always go back into your advanced account settings and point the Trash to the All Mail folder. While All Mail will adopt a trashy icon, it’s a simple way to archive data (but be sure that you don’t purge this All Mail folder since you’ll lose everything EVER).

My suggestion is to create a rule (though it isn’t as automatic). Click on the Rules button in the ribbon, and select Edit Rules. Create a new rule that tells the Trash folder to move items to the All Mail folder as seen in the screenshot below.

The rule will be applied by either visiting the Trash folder, or by clicking on Rules in the ribbon, and selecting your rule from the menu. Pretty cool huh?

Lastly, every time you check your sent mail, visit your drafts folder, or otherwise navigate your account, Outlook considers these items to be unread until you view them. I composed an email and Outlook thinks it’s unread when I look at my Sent Mail folder. Again we can create a rule to solve this issue.

Your new rule should mark most folders (it’s totally up to you) as read as you view them. I don’t need to see an indicator telling me how many unread sent mails I have — it’s only useful for knowing how many unread items are in my Inbox (and maybe your Drafts folder). It’s super handy, and you can use the screenshot below as a reference as well.

That’s All Outlook Wrote

Hopefully with a little tinkering, you can further enhance Outlook to do even more incredible things with Gmail. Personally, I’d love if Microsoft mirrored Gmail’s labels to Outlook’s categories: that’d solve a ton of problems with some creative thinking. In the meantime, it’s not entirely effortless to get Outlook to play nice with Gmail, and even after you’re done, you feel like the process should have been so much smoother. Though at this point I imagine you’re just pretty darned happy to get the two to tango, and I can’t blame you – set up isn’t exactly fun. And please, don’t even get me started on managing POP folders. Ugh!

You’re on your way to becoming an Outlook master. For more information on Microsoft Outlook 2011 for the Mac, be sure to visit Microsoft’s Getting Started Guide which will walk you through everything from the interface to the nuts and bolts. Enjoy!

If you have any other tips you’d like to share, corrections, etc., be sure to leave a comment below, and I’ll update the article if appropriate for the world to see — thanks!