How I synchronize OS X Contacts with Google Contacts and my iPhone

Abandon all hope, ye who enter here. Dante.

This one is for Martin.

I have synchronized my OS X Address Book entries with Google Contacts and MobileMe/iPhone for over a year. It mostly works. This is how I would do the Google Calendar part of it if I were starting out today. The MobileMe stuff is relatively easy [1] and I won't describe it further.

Before I begin, however, I require any reader to pass through three gates of informed consent ...

Gate 1. “Do I feel lucky?” Well do ya, punk?

If there's anything in this post you don't understand, you shouldn't try this. It could blow your Address Book apart. You might spend months reassembling it.

Gate 2. Read my 2011 resolution on managing complexity.

This is on the premature adoption end of things. It's taken about twenty years of boring, career destroying committee work to develop an incomplete and flawed standard sharing calendars and invitations. We're ten years of pain away from a similar standard for exchanging contact information.

Gate 3: Scan my Synchronization is Hell post.

Ok, you're informed. If you proceed, as a fringe benefit, you may come to understand why healthcare, a trillion dollar industry, seems stuck in the dark ages of IT. If it's hard to get address books to communicate, how much harder is it to send patient records from system A to system B? You may start to understand things like Halamka's post on a "Universal Exchange Language" for healthcare (heavens, but he's an optimist).

I use OS X Address Book as the "source of truth". That's where I add new addresses, and that's where I define what gets pushed to Google. If most of your contacts are in Google you would take a different approach.

Step 1: Buy Spanning Sync's Contact Cleaner ($5, App store) and try Spanning Sync ($25 a year, $20 if you use my referral code NXC8PS, 15 day free trial). I don't use it sync calendars, just contacts.

Step 2: Back up Address Book. Then use Contact Cleaner to clean it up; note warnings about unusual suffixes and the like. Sync works best with a first name, last name for individuals (no spaces) and a string (with spaces) for "companies".

Step 3: Define a group in Address Book that you'll sync to Google Contacts. Start small and build up. I call mine "Google Sync. Configure Spanning sync to only sync that group:

Step 4: After sync used Contact Cleaner again. Try a few reps until you're no longer getting duplicate or messed up contacts.

Step 5: As you use Google, keep an eye out for duplicates. Use Google's merge tool opportunistically. It works well, better than OS X Address Book merge.

Step 6: Over time add more names to the Address Book Google Sync group. Until you've got every address you care about synchronizing.

- fn --

[1] Apple controls both data models and they're roughly congruent, at least if you're on 10.6.6. I don't sync via iTunes because I already own MobileMe and it lets me sync to my accounts on multiple machines. The rest of my family can't sync directly because we all share one iTunes account, they have to sync to MobileMe and separately to their OS X accounts on multiple machines.

Spanning Sync contacts cleaner - a quick review

I bought Spanning Sync's Contact Cleaner for $5 from the OS X App Store.

I've used their flagship product for years to sync my OS X Address Book to Google. It's relatively expensive ($25 or so a year) but it mostly works. Since synchronization between differing data models is an impossible problem, "mostly works" is excellent.

So I was willing to give this utility a try.

Briefly, for an early product, it works pretty well. It has a few bugs, but it's definitely worth $5. The app offers to make an Address Book backup on 1st use -- that's a good idea.

I'm a pretty good test case because

• I sync my OS X Address Book to both Google (Spanning Sync) and MobileMe
• I have over 800 cards in my personal book (more in my separate corporate directory)
• I routinely define a "Family" as a "Business" to get around the first name, last name problem.
• For individuals I often link them into "Families" by use of the "Business" field to hold a family name (or, in my case, the domain name for our family)

These are the bugs I found:

1. If you choose open in Address Book, then change type from individual to business in Address Book, Contact Cleaner will crash
2. Details view for "one name" errors omits email addresses
3. Details formatting not always optimal
4. Can't manage the individual to company conversion

I'm also a bit suspicious about how it manages group memberships when it merges or alters contacts. This may just be my paranoia coming out.

Some advice on using Contact Cleaner

• Turn off all other sync while using this tool. I sync my OS X Address Book to both MobileMe (and thus to my iPhone) and to Google Contacts [1]. Just disable your network connection.
• If you edit in the Address book, save your changes (click out of edit mode) then Rescan in Contacts Cleaner. Otherwise it won't pick up your edits.
• I like to make changes in Address Book then rescan - gives me more control and I can see the full results
• Be wary if you use non-default Address Book fields. This kind of cleanup is a very hard problem.

[1] I sync a selected subset of my entire Address Book to Google Contacts. I create new addresses in OS X and then let them sync to Google. Once they sync I can safely make smaller edits on either side (esp. email address updates). I can also do merges safely on the Google side. Group assignments are independent. I define a "Family" entry as a type of "Business", that seems to work.

iTunes PDF books won't sync to your iBooks app?

You are frustrated.

You can drag and drop PDFs to the iTunes Library icon (iTunes open). They get organized into the Books section. They seem to sync to your iPhone (iPad). Except they don't. Nothing shows up.

You've tried everything. Maybe even inspected permissions.

Try this.

Open iBooks.app.

See that lovely little button that says "Books"?

Tap it.

Now you see your PDFs.

You are welcome.

PS. You can create a collection called "All" and, using Edit, tap on items, then tap Move you can put your Books and PDFs together.

Authenticate your Google Apps email - and help finish email spam

The web is overwhelmed by splogs and garbage sites full of noiseware (emphases mine) ...

Why We Desperately Need a New (and Better) Google

... Content creation is big business, and there are big players involved. For example, Associated Content, which produces 10,000 new articles per month, was purchased by Yahoo! for $100 million, in 2010. Demand Media has 8,000 writers who produce 180,000 new articles each month. It generated more than $200 million in revenue in 2009 and planning an initial public offering valued at about $1.5 billion. This content is what ends up as the landfill in the garbage websites that you find all over the web. And these are the first links that show up in your Google search results.

Google is falling, because it's trapped by its own business model.

It looks bad, just as bad as email spam was just three years ago. Today, though, email spam is dying.  The cure was clear by the late 90s, but it's taken ten years to really work. The answer was differential filtering based on the managed reputation of an authenticated sending service. Today we call that Domain Keys Identified Mail or DKIM. DKIM doesn't identify the sender, it identifies the sending service. The sending service then assumes responsibility for the sender (they know who the sender is). If the service doesn't police its users, it gets a bad reputation -- and starts being filtered aggressively.

Gmail accounts have used DKIM for a while, but Google Apps email has made do with SPF -- an inferior solution. Google has only now rolled DKIM out to Google Apps users. If you use Google APps you should enable this (it's not automatic yet). Without it the email you send will be increasingly "second class" and more likely to be filtered out.

It took about two minutes  activate DKIM for our free Google Apps family domain. We were able to use the automated method because that domain is managed through Google's Registrar partner - eNom. It sounds like it might be trickier to activate for domains managed by my favorite registrar/hosting service - DreamHost though I expect it will eventually be automatic everywhere.

We beat email spam. It wasn't that hard, though the fix did take a long time implement. It's clear we could do the same thing with garbageware sites. That fix, however, may require a company other than Google ...

Replacing a broken 3G iPhone screen: what iFixit doesn't tell you

I used the iPhone 3G Front Panel Assembly from iFixit $70) to successfully replace a broken 3G iPhone screen. I followed the iFixit assembly directions, watched a video for a related procedure and improvised when both omitted critical steps.

You shouldn't try this. I estimate the average non-obsessive geek has a 50% chance of ending up with a fixed phone, a 30% chance of ending up with a more broken phone, and a 20% chance of ending where they started less $70 or so. Once you do this successfully once the odds of success increase dramatically, but the learning curve is steep. If you insist, then please read this post carefully. It will boost your success rate to 75%.

I recommend finding someone who's done this before and paying them to fix your phone. Or see how much you call sell the broken phone for, the buyers will easily fix it. Or buy a 3G display assembly instead ($100) and avoid about 30% of the repair hassle.

I did not attempt the $40 front panel procedure. iFixit rates that as "difficult". In English this translates to "impossible".

Lastly you can pay Apple $200 and they'll do a perfect job. Keep in mind that a new 4G iPhone costs about $700 out of contract and a new working 3G is probably worth at least $350.

If you do proceed consider also replacing the battery at the same time. About half of the hardest steps are common.

I hope by this time you've stopped, but perhaps you're already committed. Or maybe you want to make a business out of this. That would make sense, especially for someone in college where broken iPhones must be common. Here's what I learned (this supplements, but does not replace, the video and the ifixit directions)

Ordering and shipping

• The front panel assembly does NOT include tools. I missed that, because I started out looking at the insane option of the "front panel" only kit. You definitely need the plastic spudger. You could use a very slender flexible knife or a scalpel blade in place of the metal spudger. I had a magnetic 00 philips screwdriver, I don't know if their's is magnetic.
• It's surprisingly hard, with a worn black 3G iPhone, to identify that it is, in fact, a 3G iPhone! Elders will need a magnifying glass.
• The model numbers on Apple's site are only for the first batch of devices. I visited Apple's site and followed their external identifier directions.
• The assembly came inside loose bubble wrap and a simple envelope; I'm surprised it made it.
• The parts don't say Apple anywhere.

Preparation

Here's what I laid out. I was able to make up for the parts I didn't order, I had an old spudger that was fine. I think the screws are all the same but I had a different bowl for each and a picture of the step behind each bowl. The tweezers and compressed air were essential. The white paper is sticker backing to hold the cursed black tape removed during the procedure. I wish I had had a magnifying glass, but I'm 51. A bright light source should suffice for the under 40 crowd.

It took me about 2.5 hours to do this with several breaks when I ran into problems. An expert could do it in under 20 minutes.

iFixit front panel assembly directions

Read the directions very carefully several times and watch the video for the similar but harder front panel assembly. This is what they left out:

• My panel came with a screw in place. Look for this and remove the screw. If you don't know this you'll discover the screw when you do the reassemby; and you'll have to take it all apart again.
• The panel has plastic covers you'll want to remove only at the time of assembly.
• The video is an edited series of cuts. It omits several key operations.
• Reassembly is harder than disassembly.
• I wore latex gloves (powder free) to reduce hand oils and sweat getting on things.
• The relevant portion of the video is from about 1:13 to 2:06. Watch that several times, unfortunately key parts were excised.
• Manufacturing changes over time. There are differences between the very first 3Gs and later models.
• There are two forms of cable connection. There's a standard pressure join and there's the iPhone destroying FPC connector (see below). When reassembling you really need to visually line up the pressure connectors. It takes a modest push to seat them; you will then feel a soft but obvious "thunk". If you don't clearly feel this they're not really connected.

The treacherous black tape

• Study this carefully before your remove it.
• At one point you are instructed to remove some black tape. This is very hard to do, I had to work one end up. A scalpel might help. Use tweezers. The tape will curl; but mine curled in a benign way. Leave the curled loop on your paper. When you reassemble, either have someone hold the phone for you or put it in a clamp of some sort. I think the best approach would use a light locking clamp to hold the tape and tweezers. Reposition it, hold it in place, try to flatten it out.

The FPC connector

As of 1/2011 there is a key image missing from the assemblydirections at "step 6". if you haven't done this before you will have NO idea what is meant by the "PFC lock"

I have tried to capture it below, but I should have used a macro lens. It is that small. The PFC lock is a 1mm x 3-4 mm white bar that sits over the distal end of cable 3 as it emerges from a black connector cover. It is shown here in the unlocked, upright position. A simple flick of the plastic spudger will flip it up. Then cable 3 will slide out.

To reinsert cable 3 I suggest using fine tweezers on the black cable sheath to push it into the black housing above until the white line on PFC cable is about at the proximal side of the black cable cover. Then flip the PFC lock down.

Good luck.

Kensington USB hub maxes out at 4 iPhones

3 kids, 2 parents = 5 iPhones (2 used as iTouch, 2 with data plan, 1 voice only).

Charge and sync is a pain. I tried connecting all five to one Kensington 7 port dome USB hub. It worked ok until the fifth connection, then the newer iPhones (4, 3GS) started complaining that they couldn't charge of an unsupported peripheral.

So four is the practical maximum for this hub. I suspect that's about as good as any hub will do.

How to reset a passcode locked iPhone

After I got home with my stolen iPhone I found I couldn't reset it. iTunes told me I had to enter the passcode. What could I do?

Cough. Ok, seriously. For the 2nd time our good friend C. has given one of our kids her ex-iPhone [1]. C. is a wonderful person, but she has been heck on iPhones. This one has a broken screen, I'll attempt a FixIt repair after I've tested the phone. I didn't want to bug C. for her passcode (after all, it could be her bank PIN too), but Apple documents a procedure for initiating recovery mode on a device that won't mount in iTunes: iPhone and iPod touch: Unable to update or restore.

Be sure to hold the home button as you connect the cable. If you do it correctly the recover dialog appears quickly.

[1] When both her brothers had iPhones, it was clear my daughter's wrath was building. That is not something any sane human would choose to face. Getting this one for free was a lifesaver.