The Perfect Email Program

by Kaitlin Duck Sherwood

People occasionally ask me what I'd like to see in the perfect email program. Some email programs have some of the elements of a perfect email program, but none has all of them. Here's my wish list:
  1. Virus resistance. While virus resistance is a broad and general topic, I would like, at a minimum, a filter condition that can examine the names of attachments, e.g.
    	if .exe is in attachment name
  2. Easy way to see all "to-do" messages nicely grouped and prioritized. The Conventional Wisdom is that you group messages by moving related messages into a folder. For example, move all messages from your manager into your "Boss" folder. Unfortunately, many (if not most) people have a hard time keeping track of their "to-do" messages (to-read, to-reply-to, to-act-on) when they are spread across multiple folders.

    It's better if you can sort them in place, in the inbox. Ideally, you'd like the inbox to show e.g. all the messages from your spouse at the top of the inbox, followed by all messages from your boss, followed by all messages from your coworkers, etc.

    I don't care what the mechanism is for grouping, as long as the "to-do" messages are visible in one place. For example, if I can set up a view that shows all the "to-do" messages in all folders at once (sometimes called Virtual Folders), grouped by what folder they're in, fine. I do want to be able to expand/collapse the folders, however, so that I only see what is relevant to my tasks RIGHT NOW.

    Another way the Perfect Email Program could do it is to let me use filters to change a field in the message that I can sort your inbox by. So for example, if the filters can change the "category" of a message, and then I can sort the inbox by "category", I'm happy.

    NB: The filters in Eudora and Thunderbird can change the Label of a message; Outlook's rules can change the Category of a message. However, it's a bit awkward to deal with them.

    • Eudora has a very limited number of labels, 15 under Mac OS and 7 under Windows. Eudora doesn't allow grouping (i.e. being able to collapse messages in a group), but it does allow sorting first by label, second by date.
    • To sort an Outlook mailbox by Categories, you have to set up a View that Groups by Categories. Furthermore, if you reply to a message that you've assigned a Category to, when you reply, the receiver will see your Category.... and there is no way to strip Categories from incoming or outgoing messages (unless you set up a macro).
    • Thunderbird 1.5 has a very limited number of labels, although Thunderbird 2.0 is supposed to allow an arbitrary number of labels. Thunderbird 1.5 has grouping in various ways, though it doesn't seem possible to group by address book. It does allow sorting first by label, second by date.

  3. Grouping by social network. I could have put this in the group-and-prioritize-in-place item above, because grouping-by-social-network works well with the above, but you don't have to have grouping-by-social-network for group-and-prioritize-in-place to be useful. I want my email client to be able to group messages by which social network the sender is in. I want to see messages from my co-workers in one bucket, messages from my family in another, etc, as noted above.

    While yes, there are some cases where someone will be in two social networks (like if you work with your spouse), those are rare and can be handled by showing messages from people in two social networks twice, once for each social network.

    It has been my experience that it is very difficult even for humans to figure out how to categorize email messages by anything else but sender; I don't think a computer will ever be good enough at it. However, there is one and only one sender for a message, and social groups are reasonably stable (in the sense that Rosario generally doesn't leave your church group on Monday, join your skydiving group on Tuesday, leave your skydiving group on Wednesday, join your company on Friday, etc.). I think computers probably can make good guesses at who is in which social group by looking at your email history: who did you correspond with and who did your correspondent correspond with? (I do still want to be able to correct the email program's choices.)

    NB: IBM and Microsoft have both done some research on merging social networks with email. I don't think they are quite to the "group by social network" feature yet, but they are getting close.

    Even if the email program can't guess at your social networks, you can still do the grouping by social network by hand. These two features make it much easier to do so:

    • A filter condition that will check if someone is in a certain address book. This allows filters along the lines of "If the sender is in my 'Friends' address book, change the category to 'Friends'". (This is much easier than generating a different rule for each friend!)

      Thunderbird 1.5, Eudora 6, and Outlook 2000 all have the filter condition "is in address book X". Thunderbird 1.5 doesn't seem to have a way to filter for "is in any of my address books".

    • One-click/one-keystroke addition of the sender of a message to a particular address book. For example, when I get a message from my cousin for the first time, I should be able to easily add her to my "Family" address book -- and so from then on, her messages should show up with the "Family" category.

      NB: Gmail has a click->dropdown-select to add to the address book. Thunderbird 1.5 takes click->dropdown-select->move-mouse-a-long-way->press-OK to put the person into the default address book.

  4. An easy way to mark messages "done". To be able to see at a glance all the messages which I need to read, reply to, or act upon, I need to be able to get messages of my sight -- to mark them "done" -- when I no longer need to read, reply, or act upon them.

    My favorite way is to have a button in the toolbar that transfers finished messages out of the inbox and into a mailbox that has the same name as the message's category. This should also be a one-keystroke operation.

    NB: Google's GMail does this with their "Archive" button.

    Thunderbird has a bug for keyboard shortcut for filing a message to a folder, and one for specifying a default folder to file messages into. If these are implemented, it will probably be adequate. Unfortunately, there doesn't seem to be any action on those two.

  5. An easy way to hide a message until some time in the future. Sometimes you know that you can't deal with a message right now. For example, if Chantelle is the only one who knows what the status of the patent application is, and she won't be back from her vacation in Bhutan until next Wednesday, you'd like to make Bob's message about the patent to disappear for now, then reappear next Wednesday.

    NB: I like to call this the "hide-until" feature instead of the "defer" feature because I think "hide-until" makes it more obvious and explicit that the message is going to come back.

  6. A button in the toolbar for "move to next message" and "move to previous message". Many programs let you use keyboard shortcuts (frequently arrow keys), but most of the people I've observed use the mouse for navigating, not the keyboard.

    NB: Eudora for Windows has toolbar buttons for next/previous message. You can set it up with Eudora for Macintosh but it's a little clunky. Outlook has this for messages open in their own windows but not in the main list-of-messages window.

    Eudora has a keyboard shortcut for next/previous message. Outlook has a shortcut, but it's different depending upon whether the index (list-of-messages) pane or the message pane is active. Thunderbird lets you use the up/down arrows, but in Threaded mode, you have to switch between left/right to view previous-/next-in-thread or up/down for previous/next thread.

  7. An easy way to visually indicate who the message was addressed to:
    • TO me and only me
    • TO me and other people
    • CC me only
    • CC me and other people
    • BCC me (me not mentioned)
    Ideally, I'd like to be able to set different colors for messages depending upon how they are addressed.

    NB: Outlook lets you color code pretty easily. Google's GMail shows different icons based on how you were addressed. If Thunderbird 2.0 allows you to group based on sender's address book, then you could use labels to color code. (This does seem like a waste of the labelling capabilities, though.)

  8. Auto-suggest. If you are working in anything resembling tech support, you might have lots and lots of canned responses to common questions. Finding the right response might be tricky if you have lots to choose from. It would be nice to have filters able to suggest (with checkboxes or some such) probable responses, with the option to either send-as-is or edit. For example, a college webmaster could have a filter
    "If the word 'admissions' is in the subject line, suggest the 'graduate admissions' response and the 'undergraduate admissions' response."
    I got to use a client with autosuggest (and had just such a filter) when I was webmaster at a major university. It was amazing. Auto-suggest can get you through email about ten times faster.

    NB: This is Thunderbird bug 151925, the somewhat less useful but still valuable reply-with-template is bug 21210. .

  9. A way to concatenate message conversations with the redundant quoted material stripped out. I think the way that Zest does is very interesting.

    NB: Eudora 6 does message concatenation and strips quotes if and only if you use preview mode. Gmail hides quoted material in a thread. Apple's and Thunderbird both pull messages in a thread to be next to each other, but don't concatenate the messages.

  10. Automatic whitelisting. I want my email program to be able to recognize people I know: who are in my address book, who I have sent messages to, and who I've gotten mail from that I didn't mark as junk. While these people should not get a "free pass", since viruses now frequently forge addresses from people I know, I do want my spam filter to be more lenient for people I know.

    To make the automatic whitelisting useful, I'd like a filter condition

    	sender is someone I know

    NB: Thunderbird 1.5 has a filter option "is in address book X", where one of the options is "Collected Addresses", but Thunderbird doesn't actually seem to collect addresses for me.

  11. Filter actions that operate on attachments. I'd like to be able to move all attachments from people I don't know into a "probable junk" folder.
  12. Filters that can score. With pass/fail filter conditions, it's difficult to write good spam filters. Usually, messages with embedded images are spam -- but not always. Usually, messages that don't have me in the To or CC lines is spam -- but not always.

    I want a filter action that will let me add/subtract points from a spam score, e.g.:

    • add 100 points if the sender is someone I know
    • subtract 50 points if the subject line contains Viagra
    • subtract 80 points if the subject line starts with ADV
    • subtract 40 points if the body contains 1-800
    • subtract 1000 points if the body contains iframe src=cid:

    and so on.

    I want a filter condition that will check to see if the spam score is greater than/less than a value, so that I can do things like:

    • if score<-100, delete message
    • if score<15, assign to z-PossibleSpam category

    Note that this is even more powerful if there is filter-by-filter import/ export: people could share good spam rules, they could be posted on Web sites.

    (I am leery of having spam rules should hardwired into popular email programs -- doing so gives the spammers a homogenous victim population that's easy to target.)

    I did some fiddling with a Visual Basic macro that does scoring (for Microsoft Outlook), and it was pretty deadly. Spambayes, which came along later, is also quite good, but is not particularly good at using information about who you know. SpamAssassin also does scoring and works pretty well.

    NB: For Thunderbird, this is bug 151622. Note that if the built-in spam filters work well enough, this won't be necessary.

  13. Easy importing of filters on a filter-by-filter basis. This would let people share the most effective filters.

    This sounds simple, but I think it is critically important. If spam filters are centrally distributed in some way -- like if Microsoft builds them into Outlook, say -- then the spammers will learn how to work around them. If everyone's email filters are different, it will be much harder for the spammers to figure out how to work around them.

    NB: This is Thunderbird bug 151612.

  14. Connection to a collaborative URL filtering service. (This one is a little tougher, as I haven't heard of a collaborative URL filter service yet.) At the 2004 spam conference, somebody made a casual comment that 95% of spam has a URL in it. This is not surprising, as the spammers have to have their customers contact them somehow.

    While you can't just penalize all messages that have URLs in them, you could build up a database of URLs seen in spam. This wouldn't help the first person who saw a particular URL, but it would help the second, third, and thirty-millionth.

    Presumably, the spammers would start to use unique URLs for each person, but that's a bit more expensive. (Expensive is good. If it gets too expensive, the spammers can't make money any more.) Furthermore, the scoring system could penalize URLs from spammy domains, even if it isn't an exact match.

I want many other things, but these are the biggies. If you want to hear about all the other things I want in an email program, contact me.
Kaitlin Duck Sherwood

Updated 17 May 2002.

Updated 5 April 2004: Added a few notes about clients that incorporate some features; added two more wishlist items (coloring based on how addressed and Zest-type concatenation).

Updated 6 July 2004: moved the spam-related items down (since anti-spam software is getting much better very quickly). Added automatic whitelisting and collaborative URL filter. Expanded on what "done" means.

Updated 13 Oct 2006: I can't believe I didn't add these here earlier! Added sort-by-social-network and hide-until.

Updated 14 Jan 2007: Updated some of the notes to reflect current Thunderbird status. Thunderbird is getting better all the time, and is my current choice for most likely to become my Perfect Email Client.

Updated 12 June 2007: Made prettier.