Monday, May 04, 2009

In Search of the Perfect Email Software

Email is as much a fact of life nowadays for most knowledge workers as opening the morning snail mail used to be. I don't know about you, but just dealing with email has lately gotten to be a time-sink and chore I don't look forward to. Anyone who can improve this situation will certainly do a lot of people a lot of good, and that's a good example of engineering ethics in my book. Part of the problem, no doubt, is my high expectations for what should happen to my email. In what follows I'm probably going to show off my ignorance and prejudices in a good strong light, but it may be worth it if something close to my ideal software ever turns up.

I'm one of those people who takes seriously the thought that months or years later after I get an email message I care about, I should be able to find it any time my computer is on, whether it's connected to the network or not. This means (unless I'm blessed with a total-recall photographic memory, which I'm not) that important emails (that is, ones I decide to keep) need to be sorted somehow and should physically reside somewhere on my laptop for access without a network connection.

Back when email was a novelty and getting three emails a day was a comparative blizzard, these requirements were easy to meet. Sorting email into files on my computer took maybe thirty seconds. But nowadays, if I skip reading my email for only twenty-four hours, when I check it again there's easily fifty or a hundred of the little jewels, only a few of which I am interested in. The rest is everything from notices about worker-training courses I don't need to offers to help princes get their money out of countries I've never been to, and worse.

I used to pride myself on doing what the older generation called "clearing my correspondence," which meant that every day, I checked out every email (at least by its source and subject line), either threw it away or filed it somewhere using the software filing routine, and got the inbox down to either zero or the two or three emails I hadn't decided what to do with yet. Filing consists of negotiating one of those multiple-level popup menus, most layers of which have so many items that I have to use the scroll function, which on no email program I've tried has a scroll bar, so I have to slide to the bottom of the visible list and stand on the mouse till the desired category comes into view, at which point I select it and sometimes have to do the whole thing over again at the next menu level (I have files within files within files, sort of like wheels within wheels). This means that filing a single email sometimes takes twenty or thirty seconds, and oh! the joy when the very next email in the list turns out to belong right where the previous one went—another thirty or forty seconds, because this time I'm mad and slip up and select "Nutcases" instead of "NosferatuTheorists"—well, in that case it wouldn't matter, but you know what I mean. So after a half hour or forty minutes of this kind of thing, I struggle back up the Sisyphean slope to a mostly empty email box, only to turn my back for a few hours and face a door-filling pile flooding in again, metaphorically speaking.

So how would the perfect email software help me? For one thing, I could use it on either of my two main computers. The way it is now, I can have part of what I want—files of old email without Internet access—only on my office computer. For some obscure reason known only to IT professionals, I can send emails with a computer-resident software like Thunderbird (or the old Eudora) only if I'm physically plugged in to my university server. If I'm anywhere else, I have to log into the internet-based software program the University runs (it's like Gmail in that respect), send an email, and copy it to myself in order to have a permanent copy that I'll later download into my Thunderbird resident software, but that adds to my already tedious task of sorting email.

Returning to the elusive purpose of describing the perfect email software, I'd better resort to bullets if I'm going to finish at all. It would:

--- Store all the email I decide to keep in an intuitive, use-frequency-based filing system (one that makes the more frequently used files easier to get at, and saves the four-layer menus for ones I access every three years or so)
--- Be accessible anywhere in the world, for sending as well as receiving, and would leave a permanent sorted record of sent emails on my machine as well as on some server somewhere
--- Would automatically figure out the procedure for getting off an email list and write the necessary messages once I put a sample undesirable email into a "get rid of this junk" file
--- Would use some kind of quasi-intelligent processing to figure out which email sources I'm really interested in and which I'm not, and would rank order these within some kind of time-based presentation, that is, most recent interesting ones first, older interesting ones later, and so on.
--- Would give me access to all emails I decided to keep, going back to the dawn of time (email time, anyway) with or without internet access

There, that'll do for starters. So far, I haven't been able to find the perfect software. None of the server-based systems will do (Gmail, Microsoft Outlook) because you have to be hooked to the Internet to find old emails, and some of them throw away old ones anyway, drat it. But the resident programs that store mail physically on your laptop can't be used to send mail except from the one server. That seems like a simple thing to fix, but maybe fixing it would violate the computer-science equivalent of the law of gravity, or something. And moving categories around so that the most frequently used folders are easy to get at doesn't sound hard. Note that I don't want to do it—I want the software to do it for me. Sure, I could reorganize my own files, but that would add a three-hour task every few months to my already excessive time spent on computer housekeeping, and I thought time saving was what software was all about. Hah.

And don't tell me to get a new email account to cut down on the junk email, either. That way folly lies, because it just trades a few months of quiet now for the heinous duty of checking more than one email account—forever. No, thanks.

Any suggestions?

Sources: If you want to know what "Sisyphean" means, check out the back story on the founder of Corinth at—he was quite a tricky guy, it turns out, and well deserved the punishment meted to him by the gods. I think some of his descendants must be writing spamware today.


  1. This is going to be a broad outline, not much room (or time) to write a full article.

    You need:

    1. An IMAP account with really big storage. I use Godaddy's Unlimited e-mail plan ($30 / yr), but you can find one to fit your needs.
    2. Thunderbird
    3. Quickfile Add-on for Thunderbird
    4. Learn how to use search, filters and Favorites folders

    I think Outlook can be used in place of Thunderbird, but I don't care for it. If you do use Outlook, you must use the Xobni plugin. I've heard a lot of good things about it and how it organizes your Outlook like friggin' magic.

    IMAP will store e-mail on the server. You can configure the IMAP server to also download a local copy of the folder to your e-mail client. Right-click on the folder in the IMAP account you want to download, click Properties, click the Offline tab and check the box labelled "Select this folder for offline use".

    The Quickfile add-on makes filing e-mail a snap. Click on an e-mail to file, hit Alt+Q and start typing the name of the folder you want to send the e-mail to. Quickfile will figure out which folder name you're going for so you usually only have to type a few characters of the folder name.

    Mark your important folders as Favorite and use the Favorite folders view (View -> Folders -> Favorite) to reduce the clutter in the folder pane down to just your favorites. If you've setup your filters correctly, important e-mail will end up in one of your Favorites and everything else in your Inbox. If you use this and Quickfile, you should be able to browse, read and file e-mail away e-mails at about a rate of 5 - 10 seconds each.

    Also turn on adaptive junk mail filters and start training Thunderbird to sort out junk above and beyond the ordinary spam.

    You will have to figure out a filing system that you will not have to fiddle with later on. If you set it up right, you should be able to find anything you want to keep with the search function. Yeah, I know this is snowballing you but this topic alone is a book length post.

    Also remember to BCC: yourself on every e-mail you send. Do not use the Save a Copy... function. When you use Save a Copy... in an IMAP server, you will upload the original e-mail out to the recipient and then upload a second copy to the Sent Items folder. Large attachments will make you want to pull your hair out. BCC yourself instead and you will only have to deal with one upload. Then create a filter to push all of these BCCs into your Sent Items folder.

    Sending outbound e-mail is possible. You could send e-mail out through a completely unrelated account and forge the From: line of your e-mail to appear as though it came from your office e-mail. It's not foolproof but it'll work at a cursory level.

    How you do this depends on how the company restricts outbound e-mails. Company policy may be more of a barrier than technical details though. Getting around the latter doesn't protect you from the former though so use your own judgement.

  2. Hi Karl-
    You should take a look at Gist ( It meets many of the requirements you lay out in this great post. I can set an account up for you to try if you are interested, just let me know -

    Gist, Inc.

  3. I tried the trial version of this Atomic Email Hunter and found that it is very easy and fast software to collect email adresses from different websites on the Internet. We have to just enter a valid URL or keyword to get the results. User can restrict those emails ID's which they donot want to be in the email database using various filtering options.

    Most important thing about Atomic Email Hunter is that when it gets email addresses from search engines the results are very accurate as compared with other email harvesting programs tested by us. After testing 5 such programs including Fast, GSA spider, etc. we made the decision to buy Atomic mainly because it uses search engines very effectively and hence identifies more sites that are actually related to the searched keyword. This generates a targeted email list instead of risking being marked as SPAM.

    For the price, it is must-buy tool for any Email Marketeer. Please donot use the generated databases to send SPAM indiscriminately, try to use the targeted collection methods of this program and then request people to opt-in for your mailer.


  4. First of all. The perfect email software doesn't exist so don't waste time and energy finding it ;). Second. I use a combination which nearly works perfect (for me). Outlook as an email software and lookeen as a search tool for Outlook. You don't have to put emails into folders you simply search them. Maybe you want to give it a try