The case against Gmail

The case against Gmail

Summary: Gmail was a breath of fresh air when it debuted. But this onetime alternative is showing signs that it's past its prime, especially if you want to use the service with a third-party client. That's the way Google wants it, which is why I've given up on Gmail after almost a decade.

The case against Gmail

On April Fool's Day, 2014, Gmail will celebrate its 10th birthday. By Internet standards, that's several generations, and Gmail is essentially a senior citizen.

To put its age into perspective: Gmail is older today than Hotmail was when Gmail made its debut a decade ago.

For the longest time, Gmail was both cool and popular, which is part of the reason Google claims more than 400 million active users of the service. Gmail's singular claim for most of that time is that it was also relatively simple and straightforward. But lately, Google's flagship service has been showing signs that it's past its prime. In particular, Gmail's losing the ability to play nicely with third-party clients.

There's always been a fundamental contradiction at the core of Gmail. Despite Google's lofty rhetoric about open standards, the Gmail protocols are undocumented and not available for licensing. Apps can perform a limited set of interactions with Gmail via its API, but if you want to build a communications app that connects directly to Gmail, you have to use either IMAP or (shudder) POP. Either way, you get a severely compromised experience. And neither configuration gives you access to calendars and contacts.

Set aside the problems with Gmail's increasingly dated, cluttered, and confusing user experience and ignore the many issues of privacy associated with a company that profiles you based on the contents of your email. For me, the fundamental requirement of a modern email service is that it allows you to access all of your data from any device, using either a web browser or a native app. That latter requirement is where Gmail is continually falling short—apparently deliberately.

For a few short months last year, just after Windows 8 was released, Windows users could connect the Metro-style Mail app to their Google account and sync everything—mail, contacts, and calendar items—using Microsoft's Exchange ActiveSync protocol. Google had licensed EAS in 2009 because its enterprise customers demanded it. But in December 2012 Google dropped EAS support for its nonpaying customers—including anyone with a free Gmail account and with a free (grandfathered) Google Apps account.

Gmail doesn't work well with Microsoft's heavyweight corporate mail client either. Outlook on Windows and on the Mac still has to connect to Gmail via IMAP, and there's no way (short of buying a third-party add-on or paying $50 a year for a Google Apps for Business account) to get all of your Gmail/Google Apps data into Outlook. You can open a read-only copy of your Google calendar, but that's not all that useful.

And it's not just Windows users who are affected. If you upgraded your Mac to the latest version of OS X, Mavericks, you might already have encountered some very unwelcome interactions between the built-in Mail app and your previously configured Gmail account—including the inability to view your messages in the Mail app as well as an unprompted download of all your previously archived messages, potentially many gigabytes worth. My friend Rob Pegoraro confirms the problem and says: "This is just not going to work. It's easier to fire one mail client than to fire an e-mail service (although's new IMAP support is intriguing), but what would I replace Mail with?"

The biggest problem with getting Gmail to work with third-party clients is that it doesn't use the same filing system they do. Most mail servers use a folder hierarchy, with new messages arriving in the default Inbox folder. They can then be sorted by rules or dragged manually into custom folders. Gmail's default message store is the All Mail folder, and then it uses labels to accomplish some of the same tasks as you get with folders. New messages are automatically assigned the Inbox label. Archiving a message simply means removing the Inbox label so it stays in All Mail but isn't shown in the same view with other Inbox-labeled messages.

When you use IMAP, those labels are translated into folders. If you used multiple labels for a message, most clients will create multiple copies, and trying to keep things in sync is tricky.

Why the misery? Google wants you to interact with Gmail in a browser window—preferably Chrome—or in one of its iOS or Android apps. The reason, of course, is so that you'll sign in to your Google account and remain checked in continuously as you use a PC or mobile device. That allows Google to collect the maximum amount of data about you as you roam around the Internet and, in theory, to serve you the most relevant targeted ads.

But that's not possible from a third-party app, which is why Google appears to be working overtime to make those third-party options as unattractive as possible.

I used Gmail extensively from 2004 until about 2008. That address was my primary personal account during most of that time. Over the past couple of years, though, as Microsoft improved its once-neglected Hotmail service, I moved back. First to an address, then to an address, and finally to a custom domain that's attached to the servers. (See this post for instructions on how to add your own custom domain to for free.)

For the past two years, I've been forwarding my Gmail address to an account, which has a great web interface and syncs effortlessly with Outlook and the Windows 8.1 Mail app, with my 3rd Generation iPad, with a new Kindle HDX, and with any mobile phone. There's even a full-featured official app on my Google Nexus 7. Thanks, Exchange ActiveSync! The only platform where is a second-class citizen is OS X, where the new Mail app uses IMAP instead of EAS for accounts, and even Outlook 2011 for the Mac is substandard. Oh well.

Anyway, I've now set up a permanent forwarder on my address, so that any incoming messages go immediately to my new preferred address, at a custom domain hosted on I've also set up the Gmail account in Outlook so that I can send messages from that address if necessary (usually to unsubscribe from some old mailing list). And I moved several thousand old messages off of Google's servers, so that my Gmail account is as squeaky clean as the day I first opened it.

It wasn't that difficult to exit Gmail. If you're interested in doing the same, follow my lead. I've posted full instructions here: How I switched from Gmail to (and how you can too)

Topics: Mobility, Cloud, Google, Microsoft, Google Apps

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      • People under 30 using clients

        Yes, there are folks under 30 using clients, but the trend is to get away from complexity. This article is interesting commentary. Google is using Microsoft tactics against Microsoft, and the Microsoft talking head is complaining about it. Ha! It makes me recall the time Word Perfect handed out unsweetened chocolate bars at a conference to display their dissatisfaction with the way Microsoft limited the memory allotted for toolbars in Windows, thereby foiling Word Perfect's attempt to compete with Microsoft's Word. So what should a person do about this email problem? Well, that's an easy one....dump Microsoft! Did everyone note how Google is unexpectedly gulping up Microsoft's networking business? Google's "other" revenue, which includes this, took a big jump up. Stock is also up :)
        • lol, as a result, MS is working Azure into everything..

          in a bit of typical microsoft, rather than remove an embattled product, MS has announced recently that they will be working Azure into their *entire* product line. Like everything else MS, they will *enforce* adoption of a product if it doesn't make it on its own..
          • Azure an embattled product?

            Really dude? In what universe?

            Look back over the last five years and compare which cloud service providers have had the most outages, and the length of those outages. The *winners* would be Google and AWS.
        • contradictory.

          So Google should pay Microsoft for activesync licenses for free users so they can connect to Outlook instead of imap which is apparently ancient for Google, but interesting for

          biased much?

          They should apparently pay Microsoft for these activesync licenses without using targeted advertising. Ignore the lack of a feasible business case and just blow money making Microsoft users happy.

          All I can say Ed, is thank good that you are not running Google or we'd all be stuck using Bing.
        • What about Linux users?

          I came across the same issues as OP but running either Thunderbird or Mutt under Linux: sync problems, label issues etc. Moreover this month I've noticed another oddity -- Gmail constantly locks out my account w/o obvious reason alerting me about unusual activity. I think matter is not just in clashing M$ but rather in tightening of users control.
          Gary Trotcko
  • unusable?

    Why are you calling outlook 2010 desktop and webmail clients unusable? They both work fine. The webmail interface is somewhat crippled in non-IE browsers but still perfectly usable - must be since I never bother to use IE with it.
  • My only two issues with

    There seems to be a 1500 contact limit. They say there isn't but I have run into the limitation over and over, and the folks in the forums give me two different answers on that front.

    Second, I can setup groups of contacts on, and they sync to Windows Live Mail and Outlook software, but in the Outlook software they show up as Categories. Well I use the Outlook software as my email client, so when I create a Category for a contact list in the Outlook software, it does NOT show up as a group up at And there is NO option to create Groups in the Outlook software, on accounts that options is greyed out, it is only available as an option on O365 accounts.

    Other than that, I love, Microsoft needs to sell it on TV.
    • 1500 Contacts

      Da**nm that's loads...
    • 1500

      1500 contacts? Seriously? What are you using the account for? A company's phone book?
    • You should be using Exchange

      If you have 1500 contacts, you are clearly way beyond the normal consumer or small business that targets. You should be using Exchange.
      Ed Bott
      • Or Outlook

        He could still use outlook, I'd think that would avoid any contact issues.
      • Ed

        Gmail works very well with thunderbird.

        As for my contacts, I don't trust a single hoster with them so call me old fashioned but I prefer a locally backed up PAB.
        Alan Smithie
      • Well

        Not everyone has the cash to run their own Exchange server. Without hardware, MS Exchange Server 2010 runs ~$1200 USD and 5 CALs run ~$400 USD. That's $1600 without hardware and backup, both of which not only take expertise but time. If you are running your own business, you really can't afford that kind of outlay... well, maybe YOU can Ed, but most can't.

        I have a family member that runs a management consulting business out of his home. He employs 2 people: him and his wife. They do well enough financially, but they don't use and Exchange server. They use Gmail and have for quite a while.
        • Would Office365 not offer exchange on the cheap

          Correct me otherwise but what about subscribing to office365 and get outlook running on hosted exchange. Is that not a cheaper option than getting an exchange server? Not to mention the skydrive/skype minutes and if you want - the latest office sw
      • re: You should be using Exchange

        > clearly way beyond the normal consumer
        > or small business that targets.

        It depends on your definition of small business. Less than 1500 contacts is a mom and pop at the most.
        none none

        It is the worst e-mail and collaboration platform ever invented.

        Only a FOOL uses EXCHANGE!!!
        • Exchange bad???

          Apparently you've never had the waterboard like experience that is Lotus Notes and Domino...
    • Groups

      The groups comment is point on. It was a compelling reason for me to choose gmail over Groups created in one environment ( or outlook '13) should flow between the two.
      Luke Skywalker
  • I'm liking gmail less and less these days

    and while outlook has made itself pretty decent, it's not awe inspiring. not making me want to switch really.
    • Gmail is

      Not bad compare to others, besides you need gmail to have youtube account, but what can you do? Its free so no complain here.