I ran into a very interesting problem during a consult last week. One of my regular clients had been working in his address book, preparing a list for mailing holiday cards.

When he was finally ready to print labels, he ran into a vexing problem and asked for my help. He would select his list, select all the cards, and choose Print, and then choose Mailing Labels under the Style menu. While the addresses would show on the preview, it would not show the address count, instead indefinitely displaying “Sorting addresses.” Printing didn’t work, and gave error messages.

I tried backing up and restoring the address book data. I tried with the same list on his wife’s Mac (synced by MobileMe). I tried cleaning the address book with Spanning Tools, a shareware toolkit for cleaning up contacts, calendars, and sync information.

Find it here: Spanning Tools 1.1

Nothing worked! I was thinking that maybe there was some invisible data corruption in his address book data, but that didn’t seem to be the case. I thought, ‘maybe there is just one record that is causing this problem, and label printing might work if I fix it.’

But how do you go through 500 addresses to find just one that has a problem? I thought back to my childhood, and some of the puzzles I remembered enjoying, and realized I could do it in just a few steps—no more than nine, in fact.

I divided his address book entries in half, and tested each half in the Print dialog. One half looked fine and gave me a proper count, but the other half still stalled at counting addresses. I was onto something! I divided the problem list in half and tested each half, repeating until I narrowed it down to one card!

I checked out the card, and found it had an extra address, with just a country. I removed the country and that address, and the holiday list was saved! My client was able to get his holiday cards out on time.


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