Modernizing The Problem


When will Apple move 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 (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 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 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 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 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 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 is perfect just as it is?


Harvey Shipley

I have just had to take a moment to tell you that I’m really impressed by your music blog. this is an excellent site.

Joshua Parker

I too love Mail but I do have to agree with Allister: “Why are my IMAP folders and the associated inbox not in the same place?” That is very annoying and that is why I tried figuring out another solution. I have several email accounts, and I forward them to my account. It is definitely not the ideal situation but it works. The downfall is that I am not utilizing Gmail and Mail to the its fullest capacity. So because I can’t stand to see 50 different folders in my sidebar, I decided that this works best for me. Furthermore, I like the little tidbits that a few people have contributed in the comments. I think it is worth trying out some of them in the workflow that I have created. Thanks for the post.

Matthew Bookspan

@Jocca – great tip!

@Gary – yes – I would love to see a Xobni for

@Leonard – sorry.


You can color tag your e-mail files in Mail, by selecting the file and clicking on the colorsync icon in the menu heading of the mail window. You can set up a whole range of colors and file away to your heart’s content. Personally I prefer the use of folders which can be synched across your desktop computers (I have three of them) and your iPhone/iTouch through MobileMe.


Couldn’t be simpler.

Yes it could. There are (at least) three fundamental sections in the sidebar. “Mailboxes”, “On My Mac” and then any IMAP accounts’ folders. Why are my IMAP folders and the associated inbox not in the same place?

In, e.g. Thunderbird, everything for an account is in one place. As it should be.


I’ve briefly tried Mail but couldn’t understand how it was treating multiple accounts. It seemed to want to combine the inboxes which seems odd.

Hit the little toggle arrow to the left of the inbox and it shows you all the accounts and mail in them. Couldn’t be simpler.


I use Gmail now, with IMAP on my iPhone as a secondary access method. I’ve briefly tried Mail but couldn’t understand how it was treating multiple accounts. It seemed to want to combine the inboxes which seems odd.

But the number one feature that Mail lacks is also lacking in Gmail – thread by *reference*. It is the only real form of threading and it amazes me how it seems to have fallen by the wayside.

As for tagging, I pretty much only use Gmail’s labels for organising unread email so I can decide what types of email to catch up on first.


After an extensive comparison of mail clients across OS X, Windows, and Linux, my entire company migrated to Google Apps. Gmail kicked all their asses.


I want to see my inbox broken up temporally, the way Outlook 2007 does it. I want to see the emails I received today/yesterday/the day before/last/week/last month/older broken up, rather than having one giant list of 1000 emails.

I don’t sort emails into folders for a reason, I don’t have that hard a time finding them, and once they’re more than a month old I rarely ever need them.

Gary R Boodhoo

my own usage of email has become very google-centric. In a sense, gmail has become an alternate front end to maps, docs, chat, notebook and calendar (technically search also, for that targeted advertising!)

The question of how to manage and edit relationships between email threads plus these additional systems is a significant one. Its a form of datamining I suppose, one which has outgrown the limits of hierarchical trees and tag nomenclatures



Write your e-mail template until satisfied. Copy it. Create a new signature in preferences and paste it in there. Next time you want to use it, select the signature from the signatures pop up list. That’s it.


What I want is to be able to have a templet email. As a real estate agents I get the same questions all the time. In Express I save the generic emails I sent out.
I just save the to the desk top. Change the dates names and presto. off it goes.
There is an ad on that does that but again I would like to see it in Mail.

Any one else have generic emails and soulutions?



I got frustrated with; It required too many plugins to “get it right” for me, poor anti-spam protection, and ultimately using so many plugins, had a tendency to make Mail go haywire. Entourage was too unwieldy and an exchange server was too costly. Our final solution was to move to GoogleApps. And quite frankly, we haven’t looked back. The only chink in the armor in the GApps suite is the lack of GoogleGears support for all of them. Sure they’ve included a lot of 3rd party service support for sync (IMAP, CalDAV), but the integration with non-Google Apps (Mail, iCal) “just isn’t the same”, largely due to Google’s own compatibility with these standards.

Matthew Bookspan

@Bob – Honestly, my guess is the list is out of date. In a future article, I’ll take a look at creating a new list.

Michael Sippey

So I’m a fan of, and use it for all of my work email. I find it to be limited enough to force me to actually be better at email. When I was an Outlook user i spent a bunch of times tweaking folders, smart folders, rule sets, etc. With and the Spotlight-based search, I live with the “three folders” rule. Inbox, Archive and Trash. The only plugin I have installed is mail act-on, which gives me a keyboard shortcut for archiving mail. (I wish had those type of keyboard shortcuts built in, but I get why not…)

Bob Smith

How current is the Hawkwings list? Hawkwings has been dead for a while now.

Matthew Bookspan

@Simon – Love it. Thanks for the feedback. I don’t have too much free time, although enough to manage my email.

@Craig – No hubris here. Just want Apple to provide alternate ways to manage email. Different strokes for different folks.

@PB – Please wait for my follow-up article – I agree that smart folders do help quite a bit. I also agree that managing your folders with your own brain works exceptionally well too.



My only gripe (so far) is that with IMAP servers want’s to download headers from all folders. My solution is to use Thunderbird.



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.



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.

Urs W. Keller

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)

TJ Draper

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!

Craig Bradley

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.

Sarah in Chicago

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.

Eric Crist

kmail is, in my opinion, one of the best mail apps around. 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?


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

Brendan West

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.

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