Introducing MailTags

Organize Your Mail

Introduction to MailTags

By Joe Kissell

When I tell people that I'm an email power user and that I use Apple Mail, I tend to get suspicious looks. Those two claims don't seem to go together. Mail isn't especially fancy as email clients go, and it has significant limitations and quirks (to put it as kindly as possible) that have driven many users to look for alternatives. I don't blame them; if I had to use Mail as Apple provides it—and I'm speaking here as the guy who wrote the book on Apple Mail—I'd lose my mind within hours.

Fortunately, I don't have to live with Apple's bizarre idea of what constitutes reasonable email functionality. I supplement Mail with a bunch of plugins that add essential missing features, improve the user interface, and let me easily automate repetitive tasks. Two of the key plugins I've relied on for years are from Indev: MailTags and Mail Act-On. With these plugins, Mail becomes not merely usable but fantastically powerful.

In this article I'd like to show you some of my favorite MailTags features. I'll do the same for Mail Act-On in a future post.

Tag, You're It

As the name suggests, MailTags lets you tag any message with user-defined keywords, in much the same way as you can tag files in the Finder in OS X 10.9 Mavericks and later. A message can have any number of keywords, which are then available when searching, creating smart mailboxes, and applying rules. Keywords can either supplement conventional filing or replace it (if you prefer to keep all your read messages in a big Archive mailbox, for instance). To apply a keyword, click the Tags icon underneath the message header (or press Command-Control-T) and type anything you like in the Keywords field. (To separate multi-word phrases, type a comma.)

Mailtags Keywords window

Keywords are great for situations like this in which conventional searching may produce too many matches to be useful. For example, I get a lot of recipes by email, but some of them don't have the word "recipe" anywhere in the subject or the body, so it's nearly impossible to search for them. I can fix that by applying a "recipe" keyword to each of these messages as they arrive—and I can even go further by adding tags like "dessert" or "vegetarian," which likewise add information that may not appear in the messages themselves. Gmail users may notice that these keywords sound a lot like labels, and they are—in fact, MailTags gives you direct access to Gmail's labels—but MailTags goes considerably further.

Besides keywords, MailTags lets you add free-form notes to any message. If I had a phone conversation with a colleague about a particular message and want to record something that was said for future reference, I can add a few sentences in a note that's attached to the message. You can also create projects (each with its own color) and assign those to messages; these can even tie into apps such as OmniFocus and Things, if you use them (I don't, so I can't comment on that integration).

To be honest, though, I don't use the tagging features of MailTags extensively; for the majority of my needs, a combination of filing and searching works fine. However, tags are just the beginning of what MailTags can do, and I find some of its other features even more useful.

Tickle Me Email

I like to keep my inbox empty (or as close as possible) most of the time. Although I don't follow Merlin Mann's Inbox Zero method, I do like to process email as it comes in, with the goal of getting it out of my inbox at the earliest opportunity. One important rule I follow, without which an empty inbox would be impossible, is "Don't use the inbox as a to-do list." More generally, I don't keep messages in my inbox merely to remind me of something (like the fact that I'm waiting for a reply from someone or need to follow up on a message next week).

MailTags has a number of features that make it possible for me to get messages out of my inbox without forgetting about them or losing track of them:

  • Tasks: When a message amounts to a to-do item, I can turn it into an actual to-do item in Reminders. To do this, I click the Tags icon, click +Task, and fill in a task name, list name, due date, alarm, and any other relevant information. MailTags adds the item to Reminders and I can then move it out of my inbox. And, in Reminders, the task includes a link to the email message it came from, so I can refer back to it for additional information with just one click.
Mailtags Keywords window
  • Events: For some to-do items, a mere reminder isn't good enough; I need them to occupy a slot on my calendar so I'll know to set aside enough time to deal with them. In those cases, I do exactly the same thing as for tasks, except that I click the +Event button instead. MailTags then puts the item on my calendar (complete with an alarm, if I so choose).

  • Tickle dates: Then there are messages with information I need to revisit for some reason in a day, a week, or a month, but that don't imply a task or an event as such. In those cases, I set a Tickle date, which is just a little bit of date metadata added to the message that makes it appear in a certain smart mailbox at a certain time. To do this, I click the Tags icon and type a date (or a date-like term such as "tomorrow") in the Set a New Date field under "Tickle." Then I use the Tickle mailboxes (much like regular smart mailboxes) MailTags adds to the Mailbox list, which show me messages whose tickle dates are within a certain range, such as "Today" or "Upcoming."

Related to tickle dates is the Awaiting Reply feature. When I send a message, I don't know whether I'll hear back in 5 minutes or 5 weeks. Sometimes I don't care if or when I hear back, but in other situations I want to make sure I don't forget that I needed a response (so I can follow up if necessary). When that happens, I add the @Waiting keyword to the MailTags dialog as I'm composing my outgoing message. Mail then keeps track of these messages (in an Awaiting Reply mailbox under the Tickle Dates heading), so I can see at a glance which replies are outstanding. When a reply does come in, MailTags automatically clears the @Waiting tag, so the message disappears from that mailbox.

Mailtags Keywords window

Power to Spare

I've mentioned that all the metadata you can add to your messages with MailTags—keywords, notes, projects, tickle dates, and so on—are available to smart mailboxes. This is true both for the special smart mailboxes MailTags itself adds, and for any custom smart mailboxes you create yourself. So, if you want to have a smart mailbox that displays only messages from your Receipts mailbox, have a "tax info" keyword, and were received within the last year, that's a piece of cake.

Likewise, rules can use MailTags data—not only as conditions but also as actions. For example, if an incoming message matches certain criteria, you can have a rule apply a keyword, set a tickle date, and file the message. That way the message never clutters your inbox at all, but it's still available to you when and where you need it.

If you combine MailTags with Mail Act-On, your options increase even further. Mail Act-On can, for instance, selectively apply the @Waiting keyword only to outgoing messages that meet criteria you specify, and lets you assign keyboard shortcuts to rules you can apply at any time (including rules that assign or remove keywords).

To learn more about MailTags, be sure to read the Quick Start Guide (PDF). And check back here for an introduction to Mail Act-On in the near future.