Adam Rice

My life and the world around me

The trouble with Mail

I’ve recently started reading Hawk Wings, a blog focused mostly on Apple’s and other personal-information programs like iCal and Address Book. I’m always keen on ways to tweak Mail, but I was moved to actually write about it by the recent post Mail’s most annoying bug. It got me thinking about all the ways Mail could be better.

When it was released with OS X 10.0, Mail was barely usable. I had used Eudora up to that point, but when I made the switch to X, I decided to leave the old OS behind completely. While Eudora was available, it did not handle Japanese; it only handled Japanese on OS 9 thanks to a plugin that had not been ported to X (I know nothing of the state of Eudora’s i18n today). I looked at some third-party alternatives, and gladly would have paid for one that I liked, but I found nothing that I liked better than Mail, so I stuck with that.

Today, Mail is a pretty good program, but it has obvious problems, and even if those were all fixed, would be solid but not innovative.

Bad/no keyboard equivalents: Mail lets you read messages one of two ways: by splitting the window into a message-list pane and a message-viewing pane, or by showing each message in its own window. My natural inclination (probably inherited from Eudora) is to open each message in its own window, but when you do this, it is impossible to use the keyboard to navigate between messages while viewing the message. You need to close the current message window, then arrow up/down, then open that message. It’s a small thing, but multiplied out hundreds of times a day it adds up. I am dumbfounded by the lack of this, as well as some of the strange keyboard commands that are there—the commands to send and check mail, two of the most common e-mail activities, are obscure and non-mnemonic.

Bad threading: Mail tries to group messages by thread, but also groups based on subject line. I have a client that uses the subject line “request” on every message he sends me, so every time he sends me work, I need to disclose an increasingly ungainly list of messages (I keep all the old ones around just because I am that way). Another weakness in this quasi-threading is that it is “flat”–it doesn’t show which message is replying to which. This is possible. Properly threaded e-mail been possible for decades. Apple should be able to figure it out.

Inclusion of .sig in body: As far as I can tell, most civilized mail clients segregate the signature line from the body of the message when you are editing. Not Mail. This means you needs to edit around the .sig, or add it back after you’ve deleted it.

Reply format oriented towards top-posters: I’m not going to say that top-posting is wicked and only evil, stupid people do it, but I don’t do it. [Update: Holy crap, look at the passions this topic arouses.] When replying to an e-mail, I try to interleave my points with the sender’s points. Mail is set up to encourage top-posting though: it places the cursor on a blank line above the quoted text, and prefaces the quoted text not with a salutation but with a more bureaucratic “on such-and-such a date, so-and-so wrote:”. So there’s that wasted blank line, and a first line that I almost invariably wind up editing (if you get e-mail from me that has that introductory line unedited, it means either that I’m really busy, that you are bugging me, or that I don’t know how to address you). Again, customized salutation lines have been around for a very long time. Mail should solve this and not assume that everyone is a top-poster. And when I want to interleave my response into the quoted text, Mail does a lazy job. The helpful thing would be to create three blank, unquoted lines with the cursor on the middle line. Mail creates one blank unquoted line. If I’m inserting a comment between two paragraphs of quoted text, there will be one blank quoted line just hanging there—it should clean that up. I think Eudora did.

Simple filtering: I use a lot of rules in Mail to direct my mail into the appropriate slots. I know that Boolean logic can get confusing, but Mail could offer an expert mode for creating rules like “If (A or B) not C” Yes, I know that Mailsmith can do this. I also know that Mailsmith has no support for Japanese. i18n is a real bright spot in Mail: before Mail, e-mail containing Japanese was a frequent PITA. I still have occasional problems with it, but the problem is mostly solved.

No queue for outgoing mail: This is another one of those Eudora features I miss. With Eudora, it was possible to write a message and queue it for delivery later (indeed, this was the default, though it was also possible to send immediately). Not with Mail: you send it, it’s gone. A five-minute grace period would save a lot of mistakes.

So far, these complaints are just of the “this is broken” variety. There are lots of ways Mail could actually be innovative.

Presentation of threads: This is one thing where gmail is out in front: it shows “conversations,” including both messages you received and sent as part of the conversation. Even if Mail would show all the messages in a mailing-list thread in one window—ideally with proper threading indicated—I’d be very happy. If it could go a step further and strip off all the detritus of footers and excess quoting, I’d be amazed.

Mailing-list handling: As long as we’re talking about mailing lists, Mail should be smart enough to recognize “hey, you’ve subscribed to a mailing list” and offer to set up special mailboxes and filters for it. Since almost all mailing lists run on a handful of platforms (Yahoo Groups, Google Groups, Mailman, and maybe one or two others), it should be possible to create special actions for quitting a list, etc, so that newbies who subscribe to a list they then decide to leave don’t post annoyed and annoying messages to the list asking “how do I leave this list?” (actually, this suggests a whole xmlrpc mechanism for managing lists, but that’s a topic for another day).

Ad-hoc mailing lists: this could be dangerous in the wrong hands, but sometimes it is useful to have a mailing list for a short period of time and a small number of people. With the right rules and actions, a mail client could emulate a mailing list well enough. There should be a quick way to set this up.

Alternate views: It could be useful (or at least interesting) to be able to view my mail database in calendrical form. Or by person. It would be interesting, for example, to see a histogram of all the mail exchanged between me and Gwen over time.


  1. Nice post. Good ideas.

    Some people are thinking already about ways to bring iCal and Mail closer together to offer the kinds of calendrical views you mention.

  2. The “on such-and-such a date, so-and-so wrote:” line drives me insane every single time that I compose an email reply, because I end up having to delete it every time. Custom openings would be nice, but an option to TURN IT OFF COMPLETELY in the preferences would make my day.

  3. I totally agree that Gmail is way better than Apple Mail at handling threads/conversations. Mail’s main problem in this regard is that it seems to identify conversations only by subject line, which means that a lot of things get lumped in together that don’t belong together. (Turns out that, according to Mail, I have had a single conversation with fifty different people on the topic “Re:” — who knew?) Gmail knows better, and only identifies as “conversations” real conversations.) Also, Gmail’s “snippets” have proven to me far more useful than I had thought they would be: in many cases, when all I need is brief answers to questions, I can get a lot of important info just by scanning the snippets without even opening the messages, and I can do it with several messages at once (which I can’t do through a preview pane).

    However, one nice thing that Mail does — that last time I checked is impossible with Entourage and (I think) Eudora — is to allow me to select multiple mailboxes, for instance Inbox and Sent, which makes the threading must more useful.

  4. I am totally with Dave2 — I am so sick of deleting that line in virtually every reply I write. I even dug around in Mail’s plist files to try to disable it, but only managed to make Mail lose track of the date and time — the line itself remained. This is something that Entourage does allow. If you’re not a top-poster, you rarely need or want that clutter — or so I would think.

  5. Good article. I’m a fan of Gmail’s conversations, but no fan of Gmail. I explored ways to get this feature into last summer, and wrote about it here:

    After almost a year, I’m still happy with the smart mailbox way of emulating this. My one gripe is that does not seem to be timezone-aware. I have a mail server in another timezone, so rapid responses series always seem to be a little confused about what got sent when, with my outgoing mail placed three hours before incoming mail from the same time.

  6. The funny thing is, Mail actually can recognize real threads. I’ve noticed this on mailing lists when a naive e-mail user will send a message on a completely new topic—with a completely different subject line—by hitting “reply” on a previous list message. It gets threaded in with the other message.

    For whatever reason, though, it also treats matching subject lines as threads. Even though they ain’t.

  7. Just as a note, you can get some converation like functions in Mail with my MailTags plugin. In addition to adding the tags feature, I’ve also set up the search function in mail to add a “Conversation” filter. When you search for a email address, and select Converation filter, it will show all emails to and from that address — providing something of what people are looking for.

  8. Hi, by coincidence my son sent this to me just as I was summarizing my frustrations with Mail compared to Entourage to MacHome Magazine. I’d need to send you the entire e mail with .pdf attachments to list the issues I’ve submitted to Apple. The text of my e mail to MacHome:

    Hello, this is my first note to MacHome after subscribing several years ago. I enjoy the magazine and benefit from many of the tips.

    Due to an unfixable corruption of my Entourage data base (the actual warning was in a window that said “Your Office Data Base is Damaged”), I had to abandon Entourage and have migrated all my personal folders (10,000 + saved messages at 1.3 gigabites) into Mail. Hours on the phone with MS did not fix the problem. So I’m in a position to compare the features of Entourage and Mail, and the latter is found wanting. I have sent lots of detail to the Apple feedback system, as noted in the screen shots below.

    Perhaps the most irritating for me is the inability to file a message to Mail personal folders without closing it, and then lots of mouse clicking and scrolling to find the file I want to put the message in. Entourage was convenient in this regard; it keeps a running record of the last dozen or so message moves and pops up the options in the “Move” menu on the message itself. One click, one scroll, and done. Am I missing a feature of Mail? BTW, several of my initial complaints (like how to set message priorities) have been solved by reading MacHome…thanks for that!

    I don’t know how to include the attachment .pdf’s with all the other detail. If you want a copy of the e mail in its entirety, please send me an e mail address and I will supply it. Since I’m stuck with Mail, anything we can do to help Apple build a more functional system is worth some time investment. BTW, I’m no geek, so much of your commentary on handling e mail is a bit over my head; I just write and store lots of e mails!


  9. For your point, “Mailing-list handling:”, most legit mailing lists have special headers to give out information for subscription, unsubscripition, archives, etc, they look like this:

    List: dadadev

    List-Archive: <;

    List-ID: <>

    List-Owner: <>

    List-Post: <>

    List-Subscribe: <;

    List-Unsubscribe: <;


    There’s nothing that would, “really” stop from taking advantage of these headers, except maybe that not *all* mailing list managers plop them in, and, it’s One More Feature to obfuscate itself – most of Apple’s consumer-level programs have this very intense, “do we really need this feature” argument within the group of developers that write the proggy in Apple Corp. itself. But, I don’t see why someone couldn’t make a plugin to have these headers show up and be clickable and do useful things. I mean, they have a plugin to allow you to use PGP – and that does a whole lot more than just format a few headers. It’s probably already around.

  10. I expect that the reason that Mail tries to group both by thread and by subject is to help with messages from Outlook users. Replying to messages with Outlook (which has vast numbers of users – probably #2 behind Outlook Express) really kills proper threading.

    I have some sympathy for the Mail developers here. You end up with the dilemma of ‘do it the correct way’ or ‘do it the way that works with other people’s broken software’. The masses often want the latter more than the former.

    However, it would be great if Mail could be really innovative. There’s a lot of interesting text classification research around – you could use that to build threads automatically, without relying on the sender to format the message correctly. OTOH, while Apple spends lots of effort on free/bundled applications, most of that is on ‘exciting’ ones (e.g. FrontRow) and not boring old (essential!) email.

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