* Gmail, Toast, and Frogs

I heart Gmail.

By Erik J. Heels

First published 04/01/2008; Law Practice magazine, “nothing.but.net” column; American Bar Association

My wife works at the hospital where I’ve had surgery three times in the last three years. When I joked that I should get a free toaster for being such a good customer, she bought me one for Christmas. Since we’ve been together (20 years in 06/2008), we’ve owned toaster ovens but never toasters. Toaster ovens are great for making lots of pieces of toast at once, cooking hot dogs, and heating leftovers. But after using the new toaster once or twice, we realized what we’d been missing: an appliance that made toast quickly and easily. In short, the new toaster is great. If all you want is one or two slices of toast, then you should get a toaster, which does the job more efficiently and quickly than a toaster oven. There is no longer a line in the kitchen as five of us queue of for toast.

About the same time I got the toaster, I decided to convert all of the people for whom I perform tech support (my parents, my kids, my wife, my office) to Gmail from various other email programs. At work, we had been using Eudora for seven years. Personally, I had been using Eudora for 15 years. When you use something for that long, whether it’s an appliance or a software application, you run the risk of becoming blind to better solutions.

I’ve been on the Internet since 1984. I have email dating back to 1990. I’ve been using Eudora since 1993. Features such as filters, mailboxes, labels, templates (stationery files), multiple accounts (personalities), and junk email detection made Eudora the number one email client for years. But then things began to change. Email morphed from plain text to rich text (HTML). Users wanted to be able to access their email from multiple computers and switched from the POP protocol to the IMAP protocol. Attachments became the rule rather than the exception.

Every year, as my Eudora mailboxes grew in size and number, I had to recreate my mailbox hierarchy and update my filters (a complex and error-prone process at best) to prevent any one mailbox from becoming too large and unmanageable. Spam seemed to escape Eudora’s filter rules, making me rely on the (server-based) SpamAssassin. And when SpamAssassin couldn’t keep up with the onslaught of spam, I had to start automatically deleting suspected spam without even checking for false positives.

And when anyone had problems with email, I got called. Whether they were using Eudora for Windows, Eudora for Macintosh, or OS X’s Mail.app program.

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

So after 15 years on Eudora, I made the decision to switch – cold turkey – to Gmail. After one full month on Gmail, here are my initial reactions.

Gmail Positives And Negatives

Multiple Logins. I signed up for Google Apps for small business. Google Apps includes Gmail (for your own domain name), Google Calendar, Google Docs, and some other applications. I purchased five accounts at $50/year/account. Oddly, Google Reader is not included in Google Apps, so I have to login separately to that account.

Consolidated Email. After configuring the DNS for clocktowerlaw.com to work with Google Apps, I configured all of my other email accounts to forward email to my new Gmail account. For example, if you send email to my MIT alumni email address (heels@alum.mit.edu), it will go to my Gmail address. I then added a custom “from” address in Gmail (like personalities in Eudora). Gmail’s custom “from” address feature is good but not perfect. It leaves the X-Sender header intact, which confuses some email clients by revealing the account’s main email address (and defeating the purpose of having a separate “from” address). Eudora’s Kill X-Sender plugin deletes the X-Sender header, thus avoiding this problem. Gmail should add a similar feature.

Email From Non-Email Programs. My routers, my file server, and several applications (including Website-Watcher and the POP3it FileMaker plugin) send email messages. It is much easier to get these email features working with a mail server that you control than with Gmail, whose POP and SMTP implementation seems squirrelly at times. Before you switch to Gmail, consider all of the non-email programs that you rely on that also need to send email (e.g. router diagnostic messages).

Google-Powered Search. Finding email is much easier now that I’m using Google’s search engine. I can build pre-configured searches into my FileMaker-based contacts database and bookmark other favorite searches. Plus I don’t have to mess with mailboxes (as in Eudora).

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

Threaded Messages. Gmail groups conversations together by subject. Which is both good and bad. It’s bad if you’re not used to it or want to edit the subject line, and it’s good for finding conversation threads. It’s odd that this feature is not optional for those who prefer unthreaded views.

Importing Email. There is no direct way to import messages into Gmail. This is a major problem. You can indirectly import email via the IMAP protocol. Since Eudora’s implementation of IMAP stinks, we imported our email into Thunderbird and then moved it from Thunderbird to Gmail. But the transfer process is slow and painful. Thunderbird frequently reports that Gmail is unable to import messages. I can rarely import more than 1000 messages at once. After one full month, I still do not have all of my old email imported into Gmail.

Labels And Filters. Gmail provides the ability to filter email, act on messages, and assign labels to them. Labels act like virtual folders. 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 email arrived from the USPTO, for example. Plus a flaw in Google’s search engine makes it impossible to search for brackets in the subject line. We use “[admin]” in the subject line of admin-related email messages (the same format used by mailing list software), but a search for “[admin]” is the same as a search or “admin” in Google’s view. Google needs to add the ability to search for special characters to fix this problem. Also, filters are not dynamic, so I’m going to have to update all of my filters after I get all of my email imported.

Disk Space. My Google Apps Gmail account comes with 25 GB of disk space. That sounds like a lot, but it’s not really. When I made the switch from Eudora, I had 17 years worth of email, 200,000 messages, using 1 GB of disk space. That’s 5K per message. Over 17 years, that’s about 32 messages per day. In the one month that I’ve been using Gmail, I have burned up 310 MB of disk space, which is over 1% of my quota. That means that I’ll use up my quota in under seven years. In other words, I was using about 600K of disk space per day with Eudora, and I’m using about 3 MB of disk space per day with Gmail: a five fold increase. The reason for the disparity is that Gmail does not allow you to delete attachments from email messages, which seems silly. I anticipate that Google (or some third party) will solve this problem in 2008.

Spam. Google does a much better job of filtering spam than I could have hoped to do on my own with a combination of Eudora (on the client) and SpamAssassin (on the server). In fact, Gmail has revealed that SpamAssassin was only masking the spam problem. In particular, my contact form (using nms FormMail) is susceptible to spam (which I’ll fix by using a better contact form).

Privacy. Many of my friends say it’s crazy to store your email on a third party server. I compared the privacy policies of Verio (my ISP) and Google and found them to be similar. If you use POP or IMAP, then your email is on a third party server (at least part of the time). And if you send unencrypted email to anyone, then it is potentially vulnerable. I decided that the convenience of not having to manage my own mail sever outweighed any privacy concerns. Maybe the shift to web-based email will actually result in encryption programs that are easy to use.

Backup.. Now that my email is in the Google data cloud, I don’t have as much data that I need to backup. On the other hand, no third party is backing up my Gmail data now. I’d like to be able to backup my Gmail account to a third party, and I’d like to see this functionality be built-in to Gmail.


Overall I am happy with my switch to Gmail. If you stick to one technology long enough, then you run the risk of being a boiled frog, unable to detect the gradual changes around you that eventually result in catastrophe. For 15 years, I used Eudora, unaware that it’s spam technology, HTML viewer, and IMAP support had become sub-par. Gmail blows Eudora away in these areas. In other areas (most notably attachment handing and templates), Gmail is still playing catchup. The world is moving to the web, so it’s not surprising to see that Qualcomm abandoned Eudora as a commercial product while Gmail continues to improve. At least it only took me 15 years to figure it out. It took me 20 years to figure out that nothing makes better toast than a toaster.

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6 Replies to “* Gmail, Toast, and Frogs”

  1. This story sounds like we are twins separated at birth. I am doing the same thing right now and any day will be my last with my good friend Eudora.

  2. Hi Erik,
    I’m considering switching from Eudora to Google Apps Gmail too (for my business). Eudora causes conflicts with other programs, and it’s just become slow having been acquiring emails since 2000.. Do you know of any updates to the X-Sender header issue? It looks like you decided upon the same method as I for importing mail into Gmail. I did a quick test of importing my mail into thunderbird and that worked without any problems so I’ll probably go about it the same way you did.

    One thing I’d like to mention, not sure if you found this out yet. But if you go on the Firefox add-ons site, there’s some really good 3rd party tools for Gmail. One that I really like is drag and drop for attaching (like we used to do with Eudora!)

  3. Eric, when I saw the title of the article in the LP magazine, I thought, “Eric is going to explain how to do this.” When I finished, I thought, “Eric has explained several reasons I don’t want to do this right now, but keep looking at GMail for improvements.” Thanks for an informative article, as usual.

    PS – I’ve owned a toaster for years, but never a toaster oven.

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