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April/May 2008 Issue | Volume 34 Number 3 | Page 22

Of Toasters and Gmail: Converting to a Better Way of Doing Things

The transition from a longtime application to a new program can have its ups and downs. But once you make the switch, you may find that your life improves, especially if you’re talking about a smoother running e-mail system.

My wife works at the hospital where I’ve had surgery three times in the past three years. After I joked that I should get a free toaster for being such a good customer, she bought me one for Christmas. In the 20 years we’ve been together we’ve always owned toaster ovens, which are great for cooking hot dogs, heating leftovers and toasting lots of bread at once. But we had never had a real toaster. Once we tried it, we quickly realized what we’d been missing: an appliance designed to make a couple of slices of toast quickly and easily. In short, the new toaster is great.

At about the same time, I went through another transition in choosing to convert from Eudora to Gmail. At work, we had been using Eudora for seven years; personally, I’d been using it for fifteen. When you use something for that long, whether it’s a kitchen appliance or a software application, you run the risk of becoming blind to better solutions. Gmail (like the toaster) made me see things in a new light.


Backing Away from Eudora

For years, features such as filters, mailboxes, labels, templates (stationery), multiple accounts (personalities) and junk e-mail detection made Eudora the number one e-mail client. But then things began to change and e-mail morphed from plain text to rich text (HTML). Users wanted to access their messages from multiple computers and switched from POP to the IMAP protocol. Attachments became the rule rather than the exception.

Every year, as my mailboxes grew in size and number, I had to re-create their hierarchy and update my filters (a difficult, error-prone process) to prevent mailboxes from becoming completely unmanageable. Spam began to evade Eudora’s filter rules, making me rely on the server-based SpamAssassin. Eventually it couldn’t keep up with the onslaught either, and I started automatically deleting suspected garbage. And when anyone for whom I’m unofficial IT guy (my office, my parents, my kids, my wife) had problems with e-mail, I got called.

In short, tech support and spam were taking over my life.

So I made the decision to switch—cold turkey—to Gmail, and I took along all the various people for whom I perform tech support, too.


The Rundown on Gmail’s Positives and Negatives

After my initial weeks of using Gmail, here are the things I’ve learned (some negative, but mostly positive).

Multiple log-ins. I signed up for Google Apps for small business (which includes Gmail, Google Calendar, Google Docs and some other applications), purchasing five accounts at $50 per year for each account. Oddly, Google Reader doesn’t come with the Apps package, so I log in to that account separately.

Consolidated e-mail. After configuring the DNS for my law practice so that it will work with Google Apps, I configured all my other accounts to forward e-mail to my new Gmail account. I then added a custom “from” address (like personalities in Eudora). This feature leaves the X-Sender header intact, which confuses some e-mail clients by revealing the account’s main e-mail address (and defeats the purpose of having a separate “from” address). Eudora’s Kill X-Sender plug-in deletes the header—Gmail should add a similar feature.

E-mail from non-e-mail programs. My routers, file server and several applications (including Website-Watcher and the POP3it FileMaker plug-in) send e-mail messages. Their features work more easily with a mail server that you control than with Gmail, whose POP and SMTP implementation seems squirrelly at times. Before you switch, consider how many of your non-e-mail programs still “involve” e-mail (e.g., router diagnostic messages).

Google-powered search. Finding e-mail is much easier with Google’s search engine. I can build preconfigured searches into my FileMaker-based contacts database and bookmark other favorite searches. Plus I don’t have to mess with mailboxes, like I did in Eudora.

Templates. In my firm, we send many standardized messages to clients. Eudora’s stationery feature allowed us to create them quickly, complete with attachments. Gmail lacks this feature.

Threaded messages. Gmail groups conversations together by subject, which is good for conversation threads, but bad if you’re not used to it or want to edit the Subject line. Oddly this feature isn’t optional for those who prefer unthreaded views.

Importing e-mail. There is no direct way to import messages into Gmail, a major problem—though you can import them indirectly via the IMAP protocol. Since Eudora’s IMAP implementation stinks, we imported our e-mail into Thunderbird, transferring it to Gmail from there. But the process is slow and painful, and Thunderbird frequently reports that Gmail can’t import messages. After a full month, I still hadn’t imported all of my old e-mail into Gmail.

Labels and filters. Gmail labels act like virtual folders. Gmail also provides the ability to filer e-mail and act on messages. The filters are good but not great. I miss Eudora’s ability to play a sound when a certain filter condition was met. We used this to indicate when e-mail arrived from the USPTO. Plus Google’s search engine makes it impossible to search for brackets in a Subject line. We use “[admin]” in the Subject line of admin-related e-mail messages (the standard mailing-list format), but a search for “[admin]” is the same as a search for “admin” in Google’s view. Google needs to add a special-character search to fix this problem. Also, its filters are not dynamic, so I have to update all of mine manually.

Disk space. My Gmail account comes with 25 GB of disk space. That sounds like a lot, but when I made the switch from Eudora, I had 17 years’ worth of e-mail, with 200,000 messages using 1 GB of disk space. And in only the first month of using Gmail, I burned up 310 MB of disk space, roughly 1 percent of my quota (which means I’ll go over that quota in seven years). Overall, compared to my use of 600 K of disk space per day in Eudora, I’m using about 3 MB per day in Gmail: a fivefold increase. The disparity results from Gmail not allowing you to delete attachments from messages, which seems silly. I anticipate that Google (or some third party) will solve this problem in 2008.

Spam. Google does a better job of filtering spam than the combination of Eudora (on the client) and SpamAssassin (on the server) that I’d been employing. In fact, Gmail has revealed that SpamAssassin was only masking the spam problem.

Privacy. Many of my friends say it’s crazy to store your e-mail on a third-party server, but I compared the privacy policies of Verio (my ISP) and Google and found them to be similar. If you use POP or IMAP, your e-mail is on a third-party server anyway (at least part of the time). And if you send unencrypted e-mail to anyone, it’s potentially vulnerable. I decided that the convenience outweighed the privacy concerns. Maybe the shift to Web-based e-mail will result in encryption programs that are actually easy to use.

Backup. Now that my e-mail is in the Google data cloud, I don’t need to back up as much data. On the other hand, no third party is backing anything up now. Because I like the added security of a third-party backup, I’d like to see this functionality built into Gmail.


Feeling on Par at Last

Despite the glitches, overall I am happy with my switch to Gmail. For 15 years I was unaware that Eudora’s spam-filtering technology, HTML viewer and IMAP support were all subpar, and I’ve found that Gmail blows away Eudora in these areas. In other areas (most notably attachment handling and templates), Gmail is still playing catch-up—but it continues to improve. At least it only took me 15 years to figure out something better than Eudora. It took me 20 years to figure out that nothing makes toast better than a toaster.

About the Author

Erik J. Heels is the principal of Clock Tower Law Group, a patent and trademark firm in Maynard, MA. He provides news and commentary on the intersection of law and technology at