Let us tell you something…

Since Apple released the 3.0 update to its iPhone; I’ve been living under duress. My wife, who is a meticulous woman, requires her calendar to be synced and available on her iPhone at all times. (Polar opposite of me; I wouldn’t survive without her.) Needless to say, when the release was pushed out by Apple on June 17th, 2009 she wanted to upgrade. After all, we’ve been craving copy-paste-undo for over a year…  So, the upgrade went… neither poorly nor well. (my upgrade was another story, not pertinent at this moment.)  I had assumed all was well, until she returned home from work on the 18th with a booming complaint. “My iPhone Calendar doesn’t have any of my meetings on it.”

We contacted our “employer’s” IT Department Help Desk; because that’s the first place to go for no reason what-so-ever.  We were informed that our employer, who supports the iPhone through their Exchange ActiveSync services, is not yet supporting the iPhone 3.0 upgrade.  So I spent the next few days trying to understand what changed with this release, after all, it worked flawlessly in the 2.2.1 release.

A temporary solution, perhaps? : June 21, 2009

I learned about all the great new features in the 3.0 upgrade; enhanced support for calDav which meant Google Calendars without a third party interface. (YAY, a solution, for the time being…)  I created an account for her with Google Calendar, and installed the Google Sync client on her PC, and set up the account information on the iPhone (as I have it installed on my iPhone) and I was pleased with myself. (Or so I thought)

It appears that my wife’s Exchange Calendar has over 1,300 appointments on it, dating back to June of 2007. (She never deletes, she’s a real CYA kind of person.) So Google Sync was choking trying to interface with the Outlook client on her PC, and after several hours, I gave up on that approach and went to bed.

A Bad Place. June 22, 2009, 8:30pm;

We had exhausted all our “logical bypasses” and came to the decision that we would both benefit from reverting the iPhone to its original 2.2.1 release. She could return to operations as normal, and I could get some sleep. Little did I realize that “Apple don’t play that game.”

Committing to an upgrade with Apple is permanent… All or nothing.  None of the Apple online support documentation referred to “downgrading” and the only things I could find on this great internet were “iPhone Hackers” – redSnow, yellowSnow.. I don’t want to Hack the phone, I like paying an exorbitant amount of money for services I can’t rely on. (re: Thank you Bright House, or Dull House? )

Rinse and Repeat. 10:57pm;

I put the iPhone in DFU mode, downloaded every version of the iPhone1,2_2.2.1 Build I could find, and attempted to restore my iPhone with no great success. I’m not a hacker by any definition. I like logic flow, and I cruise the “norms” without making waves. I spent nearly 4 hours attempting to reinstall a cell-phone OS, from less-then-reputable instructions, with no sign of support from Apple, I got a little frustrated. That’s when I started “Mashing Buttons.”

Oops, I’m F%$#d! June 23, 2009, 2:30am;

I tried resetting and restoring the iPhone everyway I could. Then I tried doing a complete “Erase All Content and Settings.” The process took an extremely long time, and even after waiting thirty minutes, with progress bar less then a third complete. I did a hard reset; holding down the Power and Home Buttons for 10 seconds. Bye Bye Electrons.

“Then, all was still. Absolutely still.” (A little ‘Magic Tree House’ reference.) The iPhone was blank. It wouldn’t turn on. I tried to DFU it and iTunes didn’t see it, it couldn’t restore, I “bricked it” (A term I learned only a few hours before while researching all the ways to hack this thing.) So I prayed. I prayed that Satan would take me from this living hell, to a warmer, muggier place like Florida. (Sh1t! already here.) It was inevitable; soon my wife would wake up to realize I had turned her phone into a $300 paperweight.

Breathe in slowly, then Exhale. 4:30am;

I decided to take a break, cool down, and return to logic to help me find a solution. If I could get her calendar to sync on my iPhone, I could just give my phone to her as part of the divorce settlement… so I tried, and that’s when I discovered something critical. After setting up her Exchange account on my iPhone, I realized that she had TWO CALENDARS; both named coincidentally “Calendar” associated with her account. And that the default Exchange settings on the iPhone only went back 1 month to sync dates.

So I set the first (Orange) calendar as the “default” calendar, and started shaking my iPhone. (I don’t know if shaking it actually did anything, but it appeared that every time I shook it, I’d get more data from Outlook.) After 20 minutes of shaking I managed to get events up to, and including October 10, 2008, but it wouldn’t go any further. Then, I removed the calendar from the Exchange setup, which deleted the calendar I just spent 30 minutes loading, re-added the calendar, and chose the 2^nd calendar as the default, and this time I set the Calendar Sync settings to “All Events” and started shaking again. That was it! I got her calendar on my iPhone. Now, let’s get HER iPhone working again.

I went back to my little grey Mac in Kealakekua. 5:45am;

I disconnected her iBrick; restarted my G5, and let it boot through to the desktop. I plugged the iBrick back in and attempted to reset the phone. While depressing the Power button and Home button for 10 seconds I thought about my children and the visitation rights I could be granted by the courts. Then I released the power button while continuing to hold the Home button until something happened! It blinked… I swear… a white flash, and iTunes perked up in my Mac Dock. I could restore once again! I’ve been saved!

I hear the shower, better hurry. 6:15am

I transformed the iBrick back to an iPhone running 3.0. I did not “recover” from an previous image, I reset is as a “New Phone.” Then I preformed my Calendar selection dance: First the Orange Calendar, Shake then purge. Then the Red One; shaken, not stirred. It took about 35 minutes in total to get the 1300+ events synced via the wireless connection in my office. Then I bounced into the master bedroom, still wired on a pot of coffee at midnight, proud to tell my wife that I was her Geek-Hero-Husband again.

As I explained the trials of the evening, it occurred to her that prior to her gaining access to the Exchange ActiveSync services, she had a local “Calendar” on her iPhone, and when she merged into the corporation’s system, she had begun suffering synch issues with her laptop, but never her iPhone. We’re guessing that when she was accepted into the Exchange Borg, her previous “Calendar” – codename: Orange, was added to her company account, thus creating two identical “Calendar” instances on the Active-Stink network. Intermittently she’d experience issues when her “Orange” calendar would take precedence over “Red” and it wouldn’t show her events on her PC. She was told by the help desk to run “Detect and Repair” whenever that would happen. (Instead of fixing the problem correctly, the Help Desk Drones just told her it was an issue with her PC.)

So what have we learned?

1. Don’t update an iPhone unless you’re absolutely certain that it’s been blessed by the Pope and IT. There’s NO going back (legitimately.)

2. Microsoft Exchange ActiveSync can not successfully sync multiple calendars of the same name, on the same user account without the occasional hiccup.

3. Help-desk phone-jockys don’t solve problems, they just catch and release.

4. Patience is a virtue; I don’t have.

5. 36 ounces of coffee ingested after 9:30pm will keep you active until 7:00am, when you can swing by Starbucks and get more. (As a good friend says, “As hard as I try not to, I keep getting blood in my caffeine system.”)