By Dan Kennedy • The press, politics, technology, culture and other passions

Tweaking Gmail with IMAP

It’s tech week at Media Nation. Fresh from foisting my video issues on you, I thought I’d give an update on my ongoing efforts to make Gmail dance to my tune.

Taking some excellent advice from a few astute readers, I set up Apple Mail to engage in two-way communication with Gmail via IMAP. As promised, this proved to be a far better set-up than accessing Gmail via POP. With IMAP, Apple Mail is more or less in constant contact with Gmail, syncing messages and folders so that what’s on my hard drive is exactly the same as what’s in my Gmail account.

One thing that surprised me after I first set up Apple Mail was that copies of all my Gmail messages (and I save pretty much everything except spam) were downloaded automatically to my hard drive. I suppose that’s the idea. But what about when an iPhone user sets up IMAP communications with Gmail? Do all those messages get downloaded to the iPhone, too? That doesn’t make much sense.

Now, here’s the best part. My biggest problem with Gmail is the way it interfaces with my Northeastern account. I had set up Gmail so that it would grab my NU mail. But occasionally there are delays of an hour or more — usually not a big deal, but sometimes critical. Also, although I haven’t found any specific examples for a while, I swear that there were occasions when important NU mail never made it to Gmail.

So, I reconfigured Gmail to stop receiving NU mail, and then set up a separate Northeastern account in Apple Mail using POP (no IMAP available). Now all my NU mail is downloaded directly to my hard drive, bypassing Gmail completely. And once I’ve got it, I can move it into Apple Mail folders that are then synced to Gmail and its labeling system. It gives me all the advantages of Gmail with none of the disadvantages.

I had hoped to be able to sync Gmail Contacts with my Apple Address Book. But to do that, you need an iPhone or an iPod Touch, or a willingness to hack your Mac. Fortunately, it was simple to export my Gmail Contacts as vCards and then import them into Address Book.

All of which means that I’ve attained e-mail nirvana, right? Well, not quite. Here are some issues that probably can’t be solved, and that I’m trying to decide whether I can live with or not:

  • Cloud computing is better than desktop computing. The single best thing about Gmail is that you’re doing everything on Google’s servers. You don’t have to worry about which computer you’re working on. And you don’t have to have a bunch of different programs open. I’ve now got Apple Mail and Address Book running pretty much all the time, and that’s on top of Firefox, NewsFire, Word and whatever else I’ve got running.
  • Gmail is more aesthetically pleasing than Apple Mail. And it’s not just aesthetics. Gmail lets you compose a perfectly formatted HTML message. Apple Mail is stuck in RTF, even though it seems perfectly capable of reading HTML. I often find myself switching to Gmail to compose, secure in the knowledge that IMAP will bring everything back together in the end.
  • Labels are better than folders. Apple Mail uses folders. Gmail uses labels. IMAP makes a seamless transition from folders to labels. But, in Gmail, you can assign more than one label to a message. You can’t do that with folders.
  • No more Gmail Chat. Not unless I fire up Gmail. I don’t use it that much anyway, but I like to know it’s there.

What’s my bottom line? I haven’t quite decided yet. In a perfect world, I would stick with Gmail on the Web, but my Northeastern account is enough of a complicating factor that a hybrid solution probably makes more sense.

One thing I have not yet done is take up another reader’s suggestion and take Mailplane for a test drive. I did poke around the site a little bit, and I’m not sure it would make my life any easier. If anyone has tried it, I’d be interested to know what you think.

For that clean, squeaky Gmail Soap feeling, click here.

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Fair use: The video (II)


Fox moves from eccentric to weird


  1. Anonymous

    Geez Louise, Dan, this is boring stuff.

  2. Dave Bonner

    Not sure which of the NU systems you’re on…departments sometimes use their own mail system. But according to you should be able to set your faculty mail account to simply forward everything it gets to gmail.”I forward my NEU email to another mail system. How can I continue to do this with the new email system?Visit and click Forward Mail. However, with expanded functionality that the new Web based system has to offer, we suggest you give it a try before you forward it! “

  3. Dan Kennedy

    Anon: Then don’t read it! Not every post is for every reader.Dave: For quite a while I had the NU system forward my mail to Gmail. It seemed like a great solution. But I found that NU people were sending stuff directly to my Gmail address, as though I didn’t have an NU address.When I looked into it, I learned that the server-based Lotus Notes address book that NU uses had incorporated my Gmail address as my “official” address. So I turned off forwarding and set Gmail to grab my NU mail. But that’s when the delays started.No perfect solutions, unfortunately.

  4. Anonymous

    The next step.Get rid of gmail chat and get some independent chat program that can communicate with everything. There are several. Pidgin and Spark are two, but there are others. With them, you enter your credentials for each chat service (GTalk, AIM, MSN, Yahoo!, IRC, &c &c &c) and it manages the lot of them. I do consulting work, so can’t enforce any particular chat on my clients, I have to be available in any one of them which would be impossible running five or six different chat programs.There’s also an online (web) version of a chat consolidator called meebo that’s pretty popular.

  5. Dan H

    You ask about gMail dumping tons of messages onto an iPhone. Yes, that’s the downside. The upside is that until the new firmware comes out, gMail is the only practical way to do mass deletes on an iPhone. Broom dozens of messages on the gMail web site, then grab mail with your phone and they disappear very rapidly.-Dan H.

  6. Larz

    Careful, Dan. That gmail stuff at NU will lead you back the the Gnus.— Larz

  7. Boston Venerable Bede

    Greetings:I encourage you to look at this post for further information on syncing Apple Address book and Gmail contacts.Link:

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