When will Apple move Mail.app into the modern world of email management? Even with version 3.5 (included with the latest OS 10.5.5 update), users of the application are stuck with some pretty cryptic email management paradigms. Why are we stuck with email folders? How about those […]

When will Apple move Mail.app into the modern world of email management? Even with version 3.5 (included with the latest OS 10.5.5 update), users of the application are stuck with some pretty cryptic email management paradigms. Why are we stuck with email folders? How about those ahem, powerful email threads? Let me elaborate…

I use both Mail.app (personal) and Microsoft Entourage (corporate) as my daily communication tools. Both are feature rich applications that apparently meet the needs for their user base. I prefer Mail.app due to its performance and extensibility (it also has better support of MobileMe than Entourage does, with respect to MobileMe accounts/email aliases).

My overall email load is probably average. I see about 10-20 personal emails per day and over 100 in the corporate environment. I do not subscribe to many lists, so this keeps my email pared down and relatively focused.

So what are my gripes?

I have quite a few. Where is the native support of email tags so that I can search by keyword or similar mechanism? Where is the native support of viewing emails by conversation? Further, where is the capability to then filter the conversation with the correct timeline by removing the out-of-sync replies? Lastly and more importantly, where is the intelligence in the application to help manage the influx of email based upon my reading and replying behavior?

It’s pretty clear that the integrated Spotlight search is useful. I can perform lightning-quick searches for my Mail.app content (Entourage 2008 supports integrated Spotlight searching as well). However, when searching, it involves extra thought about the sender, subject, timeline and more. Contrarians will note that I could build Smart Mailboxes to handles some of these esoteric queries. However, that takes additional work and has some limitations as well (although there are some great examples up on 43 Folders: “Some handy Mail.app Smart Mailboxes”).

By comparison, Gmail (a product I do not use) supports the ability to Label (read: tag) emails so that I can then filter/view and perform searches for content based upon the way I think (for example: “Personal” or “Financial”). I don’t have to spend the extra mental cycles and think: “What was the title of that email?” or “Who wrote that email?”.

A third-party product, Outspring Mail provides the ability to automatically route emails to specific folders via Bayesian filtering. I have tried Outspring Mail and can say that it is a great version 1 product, although it has a way to go to compete with existing applications and other free alternatives.

There are also a multitude of Mail.app plugins available, including MailTags, Mail Act-On and a huge list over at Tim Gaden’s Hawkwings. On a positive note, having a plugin model enables software developers to build great products. On a negative note, there is a possibility of Mail.app instability when using many plugins. Lastly, there is generally a financial penalty too. Maybe with Snow Leopard Apple will treat us to some significant improvements in email management. Until then, please wait for part two (the solution) on how I solved some of these issues (or annoyances – your call).

What are some gripes you have and what would some solutions be? Or do you think Mail.app is perfect just as it is?

  1. Honestly, I file all my messages into 6 folders: Fiancée, Friends, Family, Selling, Buying, Kitchen Sink. I have several smart folders (Fiancée would be one but iPhone’s Mail doesn’t do smart folders *yet*) for everything else, and use Spotlight if I need to find anything.

    Works for me. Quite similar to Gmail, if you consider Gmail’s labels aren’t automatic without filters, from which a reasonable facsimile can be made with Mail’s rules.

  2. tags on email are overrated, I get far to many emails a day (and I’m hardly a heavy user, we’re talking 20 at most) to waste time tagging them. If I was gonna do an organisation system I’d have them organised into smart folders based on keywords (project names etc) in the actual email.

    If your tagging email you have WAYYYY too much time on your hands

  3. kmail is, in my opinion, one of the best mail apps around. Mail.app is pretty. If only Apple would fix the things mentioned above, as well as add GPG support, I’d be set.

    Hey, kmail team, port it to OS X. Puuleeeese?

  4. This may mark me as a luddite, but I actually like the folders in Mail, as I use them for archiving. Perhaps it is a hold-over from creating folder trees in DOS that made sense to me, to using PINE (and even Netscape’s mail program back when) as a teenager.

    I use folders for archiving on my primary computer (and I do have a LOT of them, I’m a bit anal about the organisation of them), with IMAP inboxes on my multiple email accounts running through Mail (Work, Gmail, I can even have a Hotmail inbox, using HTTPMail-Plugin, which isn’t quite IMAP, but I have it up to ‘sync’ on all my macs), and then I keep the unreplied emails in my inbox till I’ve dealt with them.

    I have obviously shifted recently from using POP to IMAP, after a long time of resisting because I liked the predictability and simplicity of POP. But when I started using my iPod Touch to access my mail accounts, and was shifting between my Powerbook at home and cafes and iMac in my office, it just made sense to shift to imap.

    I am now thinking about smart-folders, which I initially resisted, but I am running so many things simultaneously that I am getting to the point of having to have some help managing things. However, my work account does not provide much in the way of storage space (ie 5-6 emails containing pdfs and I get a warning message about exceeding my limit), so what would be the point of having smart-folders if I can’t have access to them everywhere?

    The big thing I would like to see in updates in Mail is better search abilities. Particularly within the email message. I know that technically it does do this, and seriously the ability to search is one of the HUGE reasons I prefer Mail (aside from the fact that it’s just a nice simple, clean email program … hell, I think they should have left out RSS and Notes), but I have noticed often that it doesn’t find everything … I’ve often had to go looking manually for a particular email and used ‘sideways’ searches to find it.

    But, aside from improving those things that Mail already does, honestly, I hope they don’t add tons of crap on. I experienced that back when with Eudora, and it seriously killed that application for me. It’s not quite broke, so don’t try to fix it too much.

  5. You complain that setting up a smart mailbox takes time, but then want to take the time to tag every single message. There are multiple ways to manage mail. Your hubris in assuming your way is the “advanced” way is annoying. Some people might be pleased with using Mail’s rules and Smart Mailboxes and find tagging pointless.

  6. I had read this writeup on how to get threaded conversations in Mail. The functionality is right there! http://smokingapples.com/software/tips/leopard-tips-coversations-mail/

  7. You know I get along with Mail just fine, I’m living without tags, IMAP support has been great. The biggest gripe is no native support for a widescreen layout. I do use a plugin called WideMail, but I wish there was native support!

    That’s my biggest gripe with mail!

  8. I have a simple solution for threads of ALL conversation: I have made an smart malbox that includes the “inbox” and “sent messages” folders, and voilà: all messages neatly in one thread (provided you have activated the option)

  9. I personally love Mail in Leopard, not only for the standard emailing functions, but for its Notes, To Do and RSS features. Since I started using Leopard, I’ve ditched standalone RSS readers and GTD applications. It’s great having all of these functions into one application. I can create a to-do based on one specific email and have a direct link to that email from the to-do item, all within the application.

    You briefly mention the Spotlight-powered search, but you didn’t mention that you can save those searches as Smart Mailboxes right from within search. Rules also let you automatically route messages to other folders.

    I’m actually a Gmail user, and I find that, with the proper IMAP Gmail setup in Mail, I can manage my email, notes and to-dos without any problems. Mail is my own Evernote. I have tried the MailTags and Mail Act-On plugins and I found that I didn’t really use them, or need them. Simplicity goes a long way for me. For Mail users who just want the basic features, it’s easy to figure out and use. For power users the advanced features are there to utilize as well.

  10. Why would I want to think about and tag e-mails instead of using smart folders? Mail threads e-mail by subject. I haven’t used gmail in a while but isn’t that how gmail works? (If there is difference, it’s so minor I haven’t even picked up on it.) If you don’t like manual folders, don’t use them. I like them and use them because smart folders, while useful, are not actually as smart as my human brain which is much, much smarter.

    Most complaints about software are from geeks who are focused on features that hardly anybody else cares about. Mail works very similar to gmail and they are both better than good enough for me and 99% of the rest of us. Why would I want to move my mail out to another program (with possible glitches that it would involve) and learn how the new program works (for features I don’t need or want)? Oh, yeah, so that I can repeat the process when a new killer app comes out 6 months from now. Go outside and smell the roses. Life is short.



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