Update your Fastmail.fm address book from Apple Address Book

I am continually coming across useful features in my Fastmail.fm account that I have previously overlooked. For example, I now know that I can import contacts into the account’s address book. As with many mail systems, this provides several benefits:

• You can use your contacts to address messages (duh).
• Your contacts’ e-mail addresses serve as a whitelist for junk mail filtering.

Since I enabled “aggressive” filtering on my Fastmail account, having that whitelist functionality is of interest to me.

The Fastmail developers have helpfully provided a way to upload multiple kinds of contact data, so I chose vCards. They were easy for me to obtain from Apple Address Book. Here’s the basic process I followed:

1. Export existing contact cards to vCard format from Apple Address Book. You can save the vCards somewhere and delete them later; one trick I use is to save temporary data like this to /tmp so it’ll be deleted by the next time I reboot. Address Book will export multiple selected contacts to one vCard file, and Fastmail accepts this.
2. Go to Options > Upload Addresses on the Options/Settings page in your Fastmail.fm account. (Half the fun with Fastmail is wading through their exceedingly busy user interface.)
3. Click on the “Choose file” button next to the “Address book file” label.
4. Select your exported vCard file in the open dialog and click “OK” to upload it.

Fastmail has done a reasonable job of matching imported vCards to existing contacts, as long as they were previously imported from a vCard. I had some duplicates for those people who I’d added manually through the Fastmail interface before importing their vCards. Fastmail does state they try to match up contacts to reduce duplicates during the import process, but I still needed to do a little cleanup — and, unfortunately, there is no “merge contact” feature I came across.

For what it’s worth, the import process is fast, but I probably brought in under 100 contacts total, so I wasn’t necessarily taxing it.

Not all of the vCard data seems to come through and be displayed in the Fastmail address book. That’s okay for me; I have it elsewhere. In particular, I didn’t see Web addresses beyond the first one show up. Other contact information, like e-mail addresses and phone numbers, seemed to display fine. (I haven’t done an export from FM to vCards to see about roundtrip fidelity yet.)

Once you have cards in your address book, you can update them later. If you’re going to bother importing them in the first place, you’re probably concerned about keeping them up to date. Since the Fastmail software does a decent job of avoiding duplicates (in my brief experience), this shouldn’t be hard to do.

The most difficult part is sorting out which cards have been changed over time. You could re-import all of your cards, certainly. Or, you could use Apple Address Book to help find the recent changes to your contacts — whether those changes were done in Address Book or synchronized via Sync Services (perhaps from Microsoft Entourage).

Here’s how:

1. Create a Smart Group in Apple Address Book to show cards that have been updated in the last seven days. Pick a period of time that works for you; seven days works for me for the moment.
2. Select the Smart Group.
3. Select all of the cards which appear in the Smart Group.
4. Export the selected cards to a vCard file.
5. Import that vCard into Fastmail using the steps above. Your changes are now in your online address book.

While this is far more manual effort than I’d like, it’s not terrible. It’s something that I can envision doing every few months. I do most of my e-mail in a desktop application rather than on Fastmail’s Web site, so if my online address book there is a little out of date, it’s not a huge concern.