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I’ve said it before, but it bears repeating: Spotlight is a cool technology that we really, really, really want to love but that has a tendency to drive us bonkers at times. Still, Spotlight can be very useful, and one of its best features is “Smart” searches—in the Finder, in Address Book, and especially in Mail. This technology lets you assign a set of criteria to a folder, group, or mailbox and then quickly access all items that fit those criteria by simply clicking on the folder/group/mailbox. In effect, you’re saving a specialized search, but the search results are updated on-the-fly so that they’re always right at your fingertips.

This feature is especially convenient in Mail, where Smart Mailboxes let you filter tens of thousands of e-mail messages instantly. For example, I can set up a Smart Mailbox that includes all email sent from the domain; this Smart Mailbox would thus give me quick access to all messages sent to me from my Macworld coworkers—at least those using e-mail addresses—without having to create a dedicated folder for Macworld mail and then manually filing mail into that folder.

The problem with Smart Mailboxes is that they search only the actual contents of your messages: message body, headers, senders, recipients. What I’ve always wanted was a way to categorize my e-mail in Mail, much like Microsoft’s Entourage or Google’s GMail allow—or, similarly, like Apple’s iPhoto lets me do with photos via iPhoto keywords. Then I could search for messages—and, thus, create Smart Mailboxes—by categories.

If you’re in the same boat, you’ll like Scott Morrison’s free (donations suggested) MailTags 1.2 (   ). From the same developer who brought us Mail Act-On, MailTags lets you assign keywords to individual messages. The great thing about keywords, as opposed to simply moving messages to folders, is that you can assign multiple keywords to a given message. For example, if Christopher Breen sends me an e-mail about an iPod product, I can assign the keywords Macworld , Playlist , and iPod to the message. The message would then appear in Smart Mailboxes (or specific searches) that include any of these search terms, even if the actual e-mail message doesn’t contain any of these words. (In effect, it’s as if I moved this single message into three mail folders.)

In addition to assigning keywords to messages, you can also use MailTags to organize messages by project. For example, when working on Playlist’s book on iPod accessories, I would have loved to have been able to assign a project name—say, iPod Life —to all messages relating to the book, whether they be from co-workers, the publisher, product vendors, or copy editors. I could have then created a Smart Mailbox for book-related e-mail. (Some of those messages would have also been categorized as “vendor contacts,” some under “Playlist,” and so on.) Each message can be assigned to a single project and unlimited keywords using MailTags.

MailTags Sidebar
Once installed—MailTags works as a Mail plug-in, so its preferences are found in Mail’s own preferences dialog—a small tag appears in the upper-right corner of Mail messages. Clicking this tag displays the MailTags panel, which allows you to assign keywords, either by typing them in manually or by choosing previously-used keywords from the pop-up menu. (A nice touch: The MailTags “tag” icon is green if a message has already been assigned tags and gray if the message is untagged. So you can see whether or not you’ve already tagged a message without having to first open the MailTags panel.)

MailTags doesn’t stop at simple categories and projects, though. As the screenshot on the right shows, it also lets you add notes to messages, set and view message priority (which other e-mail clients can set and view, but for some reason Mail can’t), and even set due dates for responding (which appear in iCal as To Do items). The latter can be quite helpful when you get a message you don’t want to reply to right away, but you know you need to handle by, say, next Tuesday. (The message and iCal item are linked, so updating one updates the other.) You can also tag multiple messages simultaneously via the MailTags submenu in Mail’s Message menu.

MailTags Smart Mail Criteria
How do you set up Smart Mailboxes to use this new metadata? MailTags uses Mail’s own interface: The criteria menu in Mail’s Smart Mailbox dialog now includes MailTags tags as choices: keyword, project, priority, due date, and note.

One of the other features I really like about MailTags is that its features aren’t limited to mail you’ve received. When composing a new message, you get the same sidebar with the same options (see the screenshot below); this allows you to include sent mail in your Smart Mailbox searches. Even better, when replying to a message, you can set MailTags to automatically copy the original message’s keyword and project tags to your response.

You can also assign/set any of MailTags’ tags via Mail rules. For example, I can set up a rule that automatically assigns the keyword Macworld to any message sent to me by a member of my Macworld address group (even if some senders’ e-mail addresses don’t actually include “”). Finally, if you’re using Mail Act-On, the handy keyboard shortcut utility for Mail, you can “tag” messages via keystrokes.

MailTags outgoing mail

What’s not to like about MailTags? Its main drawback is that it doesn’t currently support IMAP mail. As the developer explains:

Use of MailTags with IMAP is unsupported. While it can store tags for IMAP messages locally, it will not store tags for IMAP on the IMAP server. Additionally there are other limitations and issues with IMAP mailboxes.

(One “other issue” is that rebuilding an IMAP mailbox permanently deletes all tags. In other words, if you’ve got an IMAP e-mail account, move along; there’s nothing to see here.)

But for users of POP mail and Mail, MailTags is a must-have for email power users.

MailTags supports Mac OS X 10.4 with Spotlight enabled.

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