New “Apple Peel” column on Mail at

Posted by Pierre Igot in: Macintosh
December 12th, 2003 • 5:40 am

The second column in my series of three articles on Panther’s Mail application is now up at

Apple Peel: Improvements in Panther’s Mail (Part 2 of 3)

It deals with issues regarding mailbox browsing, keyboard navigation, moving messages around, message searching and sorting, message history, and attachment and signature handling.

Feel free to comment on it below.

17 Responses to “New “Apple Peel” column on Mail at”

  1. Paul Ingraham says:

    Just read parts 1 and 2. Interesting. I looked at Mail 1.2 for about two minutes before deciding that I would have to be a masochist to adopt it — primarily because of its reliance on Apple’s still amazingly limited and clumsy Address Book. It drives me nuts that Address Book is such a great idea but so poorly implemented.

    The most important functionality in an email client for me is the ability to manage categories of recipients and group mailings. To date, no email app ever written (as far I know — it’s been a while since I’ve explored) provides the functionality I need — but Address Book and Mail conspicuously fail to offer even the most rudimentary features of this nature. I would be utterly unable to conduct my business using Mail and Address Book, not even in a kludgy way.

    For now, Entourage is still my mail client of choice, even bloated with PIM features I don’t need. However, it allows me to manage categories and mailing thoroughly enough. I despair of ever having anything better, the way things are going. I can’t imagine why better category and group mailing management isn’t in greater demand… or, if the demand is there, why developers are not answering it.

    If some app is good at these things, and I’ve overlooked it in recent years, perhaps someone will let me know. ;-) I would be delighted to abandon Entourage for something better, although it makes me cringe to think of re-establishing all those categories (Entourage will export anything BUT categories).


  2. Pierre Igot says:

    Could you clarify what your needs are exactly? I use the AB/Mail combo to manage all my work-related email as well as personal, and don’t really feel any limitations. I use AB groups for various categories of people, and have actually just found out that you can include a group in another group in AB. I use Mail rules to filter my mail based on AB groups and it works quite well.

    Just curious.

  3. Paul Ingraham says:

    The clumsiness and ugliness of the AB data entry interface aside, this is what I need Mail/AB to do that it doesn’t do (and egg on me face if I’m wrong, but I sure have not seen this functionality while I was poking around):

    Define and assign multiple categories (this contact is a friend, regular client, subscriber to newsletter B, and frequently called… whereas this client is a prospect, supplier and should never be sent any newsletter),

    Category attribution has to be pretty flexible for this to work; for instance, it’s essential to define a primary category, and it’s essential to be able to configure categories for large groups at once (i.e. change subscriber status for seventy-eight contacts without affecting their other categories).

    It’s crucial to be able to view and search contacts by category: I routinely need to see lists of “every subscriber who is also a client” or “all my suppliers who are also subscribers,” and so on. In the same way, I need to be able to define mailing groups.

    Entourage can do all that passably well. Unless I missed something, AB doesn’t do it at all.

    I could go on all day about additional functionality I wish I could get — as general rule, for instance, it seems like all email clients are absolutely lousy at handling long recipient lists.

  4. Pierre Igot says:

    Tom: the fact that messages cannot be dragged to the desktop is annoying indeed. It’s even worse: dragging a message to the left when the Mailboxes drawer is open to the right causes it to open to the left instead. Extremely annoying.

    I too had missed the ability to remove attachments initially, because Apple didn’t include it in the contextual menu. Silly!

    I don’t agree with adding fancy HTML features to Mail. To me, email is and remains a text-only medium. If I need to send fancier stuff, I send it as attachments.

  5. Pierre Igot says:

    The AB interface is a bit awkward indeed. :)

    In AB, you can define multiple groups and include the same individual in different groups. So groups can act as categories for you. Also, you can send an email to an entire group by simply creating a message to yourself and inserting the name of the group in the Bcc: field in Mail (or dragging the group icon from the Address Palette). Mail will automatically expand the group name by replacing it with the list of email addresses of the entire group. If some individuals have more than one email address, you can specify which one is to be used for sending mail in the Address Palette. (The default address for each individual is the one highlighted when you select the individual.)

    You can remove an individual from one group without affecting his/her status in other groups.

    As for searching, you can narrow your search to a given group by simply selecting that group. If you select “All” in the Groups column, the search goes through all groups.

    Of course, you can also define Mail filters (rules) where the criteria are whether the sender belongs to such and such group.

    And, as I said, you can include a group inside another group.

    All this is not ideal, but it works reasonably well.

  6. Tom Moore says:

    Great reviews, which should help Apple improve a great new email product.

    I used Outlook Express and Entourage for several years before tiring of lengthy backups (and other integrity problems) imposed by that huge single file database that cannot be read by any other application. I also realized that, while my PIM and Email finally had a unified address list, nothing else could use them. The watershed moment was an article on AppleLInks, I think, showing how either Eudora or could be used for long term archival of arbitrary volumes of messages. I figured, why not just switch? I’ve never gotten into using categories, so haven’t missed them, but that would be a nice improvement for AB and Mail. Apart from the things you’ve mentioned in this review, here are some other items that could be improved:

    It should be possible to
    – drag a message to a folder or the desktop.
    – edit at least the subject of a message to improve filing.
    – remove attachments, and now it is! I had missed that…
    – insert ordered lists and tables, especially if they could also be saved as .html files, providing a simple HTML editor.


  7. Paul Ingraham says:

    The AB groups solution definitely doesn’t have the oomph, unfortunately. All of the following tasks appear to be difficult or impossible:

    – assign a contact to multiple groups simultaneously in AB (got to drag them one by one)
    – turn group memberships on and off in the contact (that is, the group knows about the contact, but the contact doesn’t know about its groups)… this is crucial for creating exclusive categories (i.e. if you are a member of group A, you must be removed from group B)
    – assign a primary group
    – visual indication of what groups a contact is a member of, colour-coding at the least, if not text labels
    – send mail to multiple groups without address duplication
    – create new groups based on combinations of criteria (i.e. “Hmm, I need a group made of all my friends and clients, but nobody unsubscribed or recently contacted.”)

    That’s a lot of limitations. And that last one is crucial… if you have people who specifically do not want mail from you on a certain subject (unsusbcribed contacts): you have to be able to view that group, select them all, and remove them from a another mailing list en masse. That’s the only way to be sure.

    Obviously, the average home user does not need this kind of functionality from an email client — but these needs are commonplace for businesses.

  8. Pierre Igot says:

    *1* How do you assign a contact to multiple groups simultaneously without having to indicate each group manually? Sounds unfeasible to me. :) I imagine the fastest solution would be to have a row of checkboxes… but then see *2*

    *2* Exclusive memberships: This sounds like radio buttons to me. But then how do you do *1*?

    *3* Primary group: What does primary mean/imply?

    *4* Colour coding: it can be achieved in Mail using rules. But how do you assign multiple colours if individual is member of multiple groups?

    *5* Address Duplication: Yes, this can be a problem.

    *6* Dynamic Groups: Similar to “smart playlists” in iTunes. Would be handy!

    Yes, I can see how Mail fails to meet some of your needs. But it doesn’t make the AB in itself a bad foundation. The core functionality is there, and would just need to be enhanced through refinements.

  9. Paul Ingraham says:

    Yep, Entourage uses checkboxes. Radio buttons are ideal for exclusive assignment of a category, but checkboxes also work: you just have to uncheck any categories you don’t want the selected contacts to be in.

    I should have written “primary category” not “primary group.” This is how the colour-coding is selected. You, Pierre, are primarily a friend, but you also receive my newsletter. Two groups, but one of them primarily defines you.

    But I can also see the other categories, not by colour coding, but simply by a text label. Scanning down a list of friends, I can easily see which ones are also clients, suppliers, etc. Or vice versa. It just plain old says it. Nice. Vital for what I do, actually.

    Address duplication is only the most exasperating of several annoying problems with handling the mechanics of larger mailings. Some quick examples: the lack of a warning dialogue before sending out an email to more than X number of recipients (“Are you sure you want to send this half-edited message to 1800 people?” would have saved my ass more than once); the fairly harmless but odd extra step of putting yourself in the TO field before you can send a message to 380 people in the BCC field; the lack of features for manipulating or even comfortably viewing large recipient lists within the message itself; and so on.

    Yep, the dynamic assembled mailing groups concept is exactly like iTunes smart playlists. It is good idea, isn’t it? Entourage doesn’t do that… but it’s reasonably easy to do it manually once all the categories are configured and assigned.

    Yes, AB is a good foundation with the core functionality, and I can see how future versions of AB might fill in some of these gaps, but I’m not holding my breath. I’ll bet it’s two year years before it’s doing a respectable portion of what we’ve discussed here, assuming they actually do take it in that direction. Meanwhile, AB seems to be no more than a really badly implemented great idea, and a weak link in Mail’s chain — so much so that I won’t touch Mail, and am annoyed every time some other application wants to use AB!

  10. Pierre Igot says:

    In my view, the one major benefit of AB, especially over Entourage’s contact database (and others), is precisely that it’s available system-wide to any third-party application that wants to use it. As much as you are frustrated by Apple’s slow pace when it comes to implementing advanced features in AB, I am frustrated by Microsoft’s obvious reluctance to let third-party applications access the contact data. With Apple’s approach, at least we can hope that some third-party developer will come up with a pro-level solution that uses AB’s data and combines it with the advanced features that you are longing for. Now that would be cool. (I wonder, for example, if it’d be possible for a FileMaker Pro database to access the AB data.)

  11. Paul Ingraham says:

    I would be delighted to use BareBones’ Mailsmith as my email client. It does allow integration with AB, which is cool, but once again I am stunkered by the limitations of AB.

    Every time I see a program that wants to use AB, I am torn between wanting to applaud it and feeling frustrated that it won’t do me any good until AB is better. Arg. It’s very easy to see what a great feature AB will be, someday…

  12. Pierre Igot says:

    Well, Mailsmith doesn’t really do much with the AB data. What I was thinking of is more like an “AB on steroids” type of application that uses the AB data — which would be closer to meeting your needs.

  13. Paul Ingraham says:

    Yes, I see what you mean. I don’t think we’ve seen an app even start to go down that road yet?

  14. Pierre Igot says:

    No, I haven’t seen any such application yet.

  15. Ken Ferry says:

    There’s no reason a third party app, interfacing with AB, can’t do I think all of what you’re asking. A dedicated groups manager, I guess. There’s no need to wait for Apple if you can convince a programmer that there’s a market for your features.

    I think Apple Mail is already smart enough to avoid address duplication. I just tested with a few groups containing only myself and I only received one copy.

  16. Paul Ingraham says:

    Yes, I’ve been working on trying to talk a developer into it. Bare Bones Technical Director Patrick Woolsley responded like this to my feature requests for Mailsmith:

    “Such a range of services is simply not something we can reasonably hope to provide. Further, since Apple already does have the prototypes for some of the functionality, it’s entirely possible that they might use it at some point. (Please note I have no specific knowledge bearing on this, but it wouldn’t be entirely surprising either.)

    “So, useful though it might be to have “smart” contact lists of the sort you mention or the other sundry items, this would both be less valuable by being restricted to Mailsmith alone, and would take effort away from other more email-related features that we would like to add.”

    I sympathize with his position. If they do it, it’s entirely possible that AB will duplicate the functionality soon after and render their efforts obsolete.

  17. Pierre Igot says:

    In my view, the solution would be a stand-alone application, not something that’s part of an email client or whatever. It would be a separate utility that manipulates the data provided by AB and communicates with the default email application when it comes to actually sending out stuff.

    It should be possible.

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