Monkeys Typing Shakespeare

The other day the monkeys were flinging more poo than usual. I walked up to a few of them as they were jumping around a computer screeching and banging on the screen. It seems Bongo had purchased a new iPhone and was trying to get it to sync with his Outlook 2003 calendars and contacts. There was very little hair left on his head as he had pulled most of it out dealing with the fine folks at Apple.

First, he was getting a strange error (0xE8000025) whenever he attached the iPhone to his PC. Then his phone would just disappear — not the real phone, the link in iTunes. He dutifully followed the Apple Geniuses advice and went the Apple Genius Bar at an Apple store. Why? I have no idea. The problem was with his iPhone connecting to HIS PC.

After about 12 hours of Apple Geniuses, Teir 1 support (1-800-myiphone), Tier 2 support, Googling every page in the known universe and using an entire bottle of Windex to wipe monkey poo off his monitor, we got his iPhone to sync.

Through our adventure, here is what we learned:

1. The iPhone needs a USB 2.0 port — if you only have USB 1.1 you may get the 0xE8000025 error when you plug in or the annoying “iTunes could not connect to the iPhone because an unknown error occurred.” Since Bongo had an older computer we added a USB 2.0 card and we stopped getting this error and the disappearing iPhone routine.

2. iPhone requires iTunes to sync. After installing it, you need to run Outlook at least once. iTunes uses the local *.pst OR (this “OR” is really, really important) the local *.ost file from Outlook. *.ost files are created when you have Exchange in “Cached Exchange Mode.”

3. To sync information from an Exchange server you must check the “Use Cached Exchange Mode” in the email setup dialog box (Tools –> Email Accounts –> View or Change…). You must also be sure that Outlook has fully synced with the Exchange server to update the *.ost file on your local machine. You can see this from the icon in your system tray.

4. iTunes deserves a lot of the monkey poo tossed at it for a problem dealing with repeating calendar events. We ended up deleting all of these (In Outlook 2003: View –> Arrange By –> Current View –> Recurring Appointments). For good measure, we also deleted all calendar events prior to the start of the year. However, I think this was probably unnecessary and overkill.

In hindsight, it would have saved a LOT of time if the Mac Geniuses or the Teir 1 support person had told us about the USB 2.0 issue. Props to Tier 1 Susan in Toronto for explaining that one to us (I want my t-shirt). It would also have been a nice thing if the < Tier 2 had told us about the *.pst/*.ost issue. We figured that one out talking to Susan. She wasn’t an Exchange expert but when she told us that iTunes actually reads through the entire file, something just clicked — without Cached mode, this file does not get updated (or created).
Bongo now loves his new iPhone with anti-monkey poo screen… me, I’m loving my BlackBerry Curve with wi-fi. I got a post about that coming soon.