People have a lot of email addresses, but sometimes they prefer to use one over the other. I generally like to send email to people using the address they last used to write to me (e.g., students have an official university email account, but also a gmail account, etc.). The Mac OS X Address Book has its own ideas about this, and sometimes it won’t pick the right one.

Oddly enough, there is a setting in the Address Book for primary email and phone, but there is no way to change this setting from the Address Book itself. I found two plugins that appear to have promise. They both do basically the same thing. Once the plugin is installed, go to an Address Book card, right-click on the email address (when the card is not in editing mode) and choose “Make primary” (or observe that the card “is primary”).

The first is the Set Primary Addresses plugin by Robert Stainsby, which I have used in the past, I thought successfully. It currently requires that you run Address Book in 32-bit mode, but that’s do-able.

The second is the Address Book plugin from ProjectWizards (created in support of a program they sell) that does the same trick, and doesn’t seem to require 32-bit mode.

However, this didn’t seem really to solve the problem. Sure, now I can make different email addresses primary, but Mail.app itself doesn’t seem to make use of this information. The best I was able to do was to set the address in the Address panel (Window -> Address Panel, or Command-option-A); for people with multiple addresses, you can pick which one you want to use and it will remember your choice. It only works from the Address panel, though; if you start typing in a person’s name in the “to” field, it will still list the options in a fixed order (shortest first?) with the first one as default, regardless of what is set in the Address panel or what is set as primary.

This seems kind of dopey to me. It looks like the choice in the Address panel does stick, so perhaps I can train myself to address my emails with that, though it requires extra keystrokes to call it up and dismiss it. Any ideas about how to make this work with the primary address are welcome.

Addendum: I think that the (not very intuitively named) “Edit distribution list” will perform the same task that the Address panel does in Mail. But it seems to still only take effect when you send to a group that includes the person. Dragging the person’s address card into a Mail message does not seem to respect this choice.

Is this really such a weird thing to want to do?

I use Mac OS X’s built-in Mail.app, and I’m pretty happy with it. The searches are quick, it does what I need, it’s integrated with the OS, and there are plugins.

Along with Mail.app, there are a couple of things that I definitely would not want to be without:

MailTags: This allows you to add keywords to your mail, and build smart folders based on those keywords. It also lets you change the color of mail messages, assign them to a project category, add to dos and events from within Mail, add notes, set due dates.

MailActOn: This lets you quickly run scripts or rules on selected mail messages. I’ve set my trigger key to ` and so I can do things like “file in McGill folder” by just hitting `m. Nice.

SpamSieve: Quite an effective spam filter plugin. And you can’t beat the company name.

MailFollowUp: Adds a “followup” option to the message menu, allowing you to do something like replying but to your own messages.

MailRecent: Adds a “move to recent” menu (better than Mail’s own, which just allows access to the last mail folder, not the last few).

I’ve also written a nifty autofile Applescript that I use, which lets me choose in the Address Book entry for people what folder I want their mail to go in and what tags I want to assign. I posted it to the indev support forums, though it seems not to have generated any discussion at the time I’m writing this now.

At this point, I have not been archiving email outside of Mail.app, but if I get to a point that I want to do this, EagleFiler is probably the best solution so far.

A good place to stay up to date about what’s available for Mail.app is hawkwings.net.