This is awesome, of course, except when it’s not. So here’s how you can sort and remove out-of-date or incorrect addresses. Your less-plentiful autofill options will be your reward.
To get started and see what Apple Mail has been storing for you, choose the menu item Window > Previous Recipients.
That’ll bring up a nifty (and sometimes quite long) list of everyone you’ve ever sent an e-mail to, whether you’ve created a contact card for them in Address Book or not. It’s like an archaeological dig through the layers of your past.
Hopefully your past won’t be as blurry as mine.
There are a couple of things you can do with this information. First of all, note the leftmost column in my screenshot above—if there’s an image of a card there, you’ve already stored the contact info for that person in your Address Book. So you can tell at a glance who made your friendship cut and who didn’t. Sorry, dude who bought me pizza that one time.
As in other places around Mac OS X, you can click any of the column headers to sort by that column. Click the name header to sort by last name, click the date header to sort by date, and so on. But you can also click the header for that first column to sort the folks you have as contacts from those you don’t, which makes it pretty easy to add the missing people to your Address Book.
If you want to go ahead and add someone new to your contacts from this list, select the person and click the Add to Address Book button. You can also click on someone and choose the Remove From List button if you no longer want that address to autofill when you’re composing a message. You don’t have to add or remove folks one by one, either—just hit Command-A to select the entire list first, or hold down Command and click on different people to select a few at a time.
Decisions, decisions.
Finally, you can remove an address right from someone’s message if you want to. Hover over an e-mail address in a message’s header to get the familiar drop-down arrow first:
Then click it to choose an option for that address.
If the person in question has an entry in your previous recipients list but isn’t in your Address Book, you can take him out right from that menu. You can alternatively choose to add him to your Address Book, create a Smart Mailbox for his messages, or start a new e-mail to that address.
It’s simple! Elegant! Useful! Not particularly intuitive! What? I’m trying to maintain a semblance of journalistic objectivity here. Are you falling for it?