I like keeping a comprehensive an accurate addressbook that includes all past email addresses for my contacts, including those which are no longer valid. I do this because I want to be able to see conversations stretching back over the years as originating from that person.

Unfortunately this causes problems when sending mail sometimes. On macOS, at least as of El Capitan, neither the Mail application nor the Contacts application have any mechanism for indicating preference-order of email addresses that I’ve been able to find. Compounding this annoyance, when completing a recipient’s address based on their name, it displays all email addresses for a contact without showing their label, which means even if I label one “preferred” or “USE THIS ONE NOW”, or “zzz don’t use this hasn’t worked since 2005”, I can’t tell when I’m sending a message.

But it seems as though it defaults to sending messages to the most recent outgoing address for that contact that it can see in an email. For people I send email to regularly to this is easy enough. For people who I’m aware have changed their email address, but where I don’t actually want to send them a message, I think I figured out a little hack that makes it work: make a new folder called “Preferred Addresses Hack” (or something suitably), compose a new message addressed to the correct address, then drag the message out of drafts into the folder; since it has a recent date and is addressed to the right person, Mail.app will index it and auto-complete the correct address in the future.

However, since the previous behavior appeared somewhat non-deterministic, I might be tricking myself into believing that this hack worked. If you can confirm it, I’d appreciate it if you would let me know.