How to Add Address Book Contact Pictures

I seem to know a billion people. Not really, but with over 2,000 contacts in my address book (which undergoes regular pruning)… it might as well be a billion.

Since I’m visual in nature – preferring to wait for the movie over reading the book, unless that book has lots and lots of colorful pictures in it – I also appreciate having avatars / photos for every contact that pores into my inbox and sits inside my address book to boot.

This shouldn’t be a problem, right? Yeah, well – in a perfect universe, we’d all be able to poop chocolate. And, I suppose, in many ways, it’s easier to poop chocolate than it is to get your address book in order in any environment that extends past one piece of software.

Chris Conveys an Emotion
This is how I feel.

Here’s my scene, if you can dig it: I use a managed Exchange 2007 server to host my contacts, but I’m also a Mac user who has come to discover that every single PIM that Microsoft has produced for OS X is absolute poop. This includes the sluggish Outlook for Mac, which I wouldn’t recommend to anybody. Not that I ever loved Entourage (absolutely NOBODY did).

So, I use, Address Book, and iCal – and was quite happy when Exchange was finally supported on the Mac desktop. Kinda. It doesn’t really work all as well as Apple would lead you to believe. I don’t want to manage two [same] contact lists on one computer, so the only way to effectively sync the Address Book to Exchange without duplicating local contacts is by using a hack known as Plaxo. I call it a hack because they’ve not done much with fixing outstanding bugs in, say, since the last time I took a chocolate poop.

So, I have Plaxo syncing the Mac data (Calendar, Contacts) to the cloud, and I have a VM of Windows 7 running Outlook 2010 on another Mac do pull data from Plaxo into it. Yes, as much as it pains me to admit: Plaxo (Comcast) has been the best glue I can find.

And let me just say that the MobileMe contact sync has been an absolute nightmare to deal with. I couldn’t figure out how some of my contact fields were disappearing. I was ready to blame Exchange or Plaxo but, as it turns out, MobileMe eats contact fields for breakfast. Only after I turned off this sync point did things get better.

But, back to the contact picture / avatar dilemma. Neither Outlook nor the Mac Address Book are very intelligent. They’re downright stupid, actually – and I’ve had to rely on several pieces to put together a complete picture. So to speak.

Many people in my address book are also on Facebook, so this utility will automatically sync their birthdays and profile imagery. If you’re thinking that the Facebook iPhone app has a contact sync, you’re right – and I’ll come back to that in a bit.

I’d hope to see the following features in AddressBookSync at some point: the inclusion of other possible vCard metadata, the ability to add Facebook friends who aren’t already in your contact list, the auto-categorization of Facebook Friends Groups into local Groups, etc.

Apparently, there are tons of people in my address book who aren’t on Facebook (or, at least, I can’t or don’t want to connect with them in any social network). They remained avatarless for a few moments, until I got the bright idea of searching for a Gravatar conduit.

Everybody. Needs. To. Set. Up. A. Gravatar. Right. Now. You essentially associate all of your email addresses with an image which is used by a growing number of services (like for the moment). It’s a globally-accessable avatar.

Indeed, I discovered something called Picture Finder. While it’s extremely powerful, insofar as its ability to display a person’s Gravatar, Wavatar, QR Code, etc. – it’s also not great for managing contact lists over 99 people. Still, it was better than nothing – and I was able to generate some fun little avatars for people who didn’t have any photo currently associated with themselves in my address book.

I’d hope to see the following features in Picture Finder at some point: the ability to auto-populate contacts without gravatars with a gravatar type of your choosing en masse, and… yeah, that’s about it.

You see, despite its functionality, I gave up after manually processing ~100 contacts. I needed to find a better way to cull gravatars for people who have registered them. AppleScript to the rescue! The aptly-titled Gravatar to Address Book Pictures worked wonders… until it got to a point when it crashed. I have no idea why it crashed – do I look like a developer to you?

For on-demand Gravatar pulls from within the address book, by the way, the Address Book “Gravatar bundle” is also available for download.

I still have too many people in my address book that are iconless – and that’s (really) driving me bonkers. If I was an AppleScript wizard, I could likely fix the problem in two shakes of a lamb’s tail.

Are you ready for the insult? Plaxo somehow eats the images before it syncs to Outlook / Exchange! So, all of my hard work on the desktop is pointless when it comes to viewing the same contacts on my iPhone. I don’t sync via the Address Book, remember – I use Exchange for that. One contact list is all I’m trying to maintain!

So, since my contact information pipeline is disgustingly busted, I had to resort to using the Facebook iPhone app to sync photos to contacts in my address book on the iPhone (which, again, is the same contact list sitting in my Exchange account). That worked well enough – for now.

Since I need to keep Outlook open anyway [*grumble*], I tried the new Outlook Social Connector extension – which, for what it is, works quite well but falls short of being insanely useful. Typical Microsoft. You can’t configure settings to keep it from spilling insane amounts of crap into new folders, you can’t sync contact pictures from the social network providers to your address book contacts, you can’t automatically sync contact lists with Facebook, and… MySpace? Who the f*ck wants to correspond with anybody who still posts updates there?! Judging from the lack of updates from that idea, I’d say it’s dead.

I did find a handful of interesting duds Windows utilities, but each one of ’em crashed before I could do anything. If you’re interested, I wielded OutSync and Synrc.

The solution? For Plaxo to stop eating contact pictures, support Facebook and Gravatar for contacts outright, for it to support Exchange without needing to go through Outlook (a complaint that has resulted in a combined two-star rating in the iPhone app store), and to update their software more frequently. I’m a Premium member, not looking for a free ride. Seriously – they’re the best game in town for what I’ve been trying to do.

And while I’m on the subject, WTF is up with the Mac Address Book still not being able to export or import a simple CSV (or tab-delimited) file?! If that’s what you need, Mail Scripts works wonders. There’s also Hubi’s Address Book Scripts, although I wish he’d make one that would help eliminate duplicate data even if they happen to sit in different fields.

Maybe an enterprising Windows / Outlook developer will help that side of the equation?

Don’t even get me started on how to eliminate address book duplicates. That’s a different matter entirely (for a completely different post, once I find the best solution for the problem).

3 thoughts on “How to Add Address Book Contact Pictures”

  1. I’ve got the same thing on my mind right now but even worse. I’ve got about 10 accounts on 5 services that I can export the lists from and there’s about 5000 contacts between them all that I can get emails for. I’m just going to make a static HTML page with a textarea to paste whatever format the export and copy the emails out of it to a list on the right with a regex and check for duplicates. I’m not sure how I’m going to go about re-importing that list to all the services to get them synced but I guess I can worry about that when I get to it :S

  2. Dude! Killer post. You’ve just helped every person who’s looking for a solution to this problem. Unfortunately you had to wield a dozen different apps, and there different operating systems to sort out this mess. I’ve been trying for years to poop chocolate, but didn’t have any success until I started reading your blog 😉 bravo Mr. Pirillo! Excellent post!

  3. I share the frustration over contact management, especially when you’ve got a lot of contacts. I’ve been following your content for years Chris, thank you 🙂 I just thought I’d share something that helped me recently. There are a lot of services out there to sync contacts, there are some that even improve your data a little but they only work if your contacts are on one network or another. If you have 1000s of contacts, there’s a good chance that a large percentage are out of date. Old numbers, emails, addresses, etc. I think the only way to truly clean your data is to ask your contacts “is this information still current?” But… if you have a lot of contacts, it can take a long time to email them, showing each the info you have for them.

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