Modernizing Mail.app: The Problem

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?

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