ARRGH! iPhone & iCal Server

I hate technology.  I really do.  Why can’t things just work?  Here is my latest bug: My iPhone will not allow me to anything other than read my iCal  server calendar.  After the jump you can read about how I got some delegated calendars to work and what the current issues are with iCal Server.

First of all let me say this: iCal Server is no way ready for primetime enterprise deployments.  I would even shy away from using it as a calendar server for a small workgroup.  There are far too many issues for it to be useful.  The biggest issue would surround invites – but for the purpose of my implementation, it’s all about sync’ing with the iPhone, baby.

For about a year now I’ve been playing with the idea of setting up a family calendar that would allow you to do all those wonderful things you can think about doing with a shared calendar.  I thought it would be a great idea since I have school aged children and I’d like to give them some experience in using some sort of online/digital organization tool.

I’ve tried installing the open source version of iCal Server, the Darwin Server, on Ubuntu and was able to get it running.  Let’s be honest here – I wanted to have a GUI interface so that I didn’t have to be mucking around with the command line.  Besides, I wanted some sort of directory system as well… and again I really wanted a GUI for all this.  So I scrapped the Ubuntu server idea and then I wasted a few months thinking about how to get a calendaring system into Microsoft’s Windows Home Server.  (Still a viable idea.. just I’m too damn lazy to pursue and would it make any money? I mean how many homes are actually using the Home Server?  Fill this under: Great ideas to let someone else get rich on) 

I finally got my hands on Leopard Server and decided to install it on an old G5 I have.  It took awhile to install — however, I ended up with a nice compact workgroup system that had a Apple-ish GUI to start my Family Calendar.  So I created all the necessary user accounts, went through the paper calendar and my wife’s ‘master calendar’ stored in iCal on her MacBook Pro, created a number of calendars that belong to my wife’s account (given that she is the cruise director of this ship.)  All in all it took about a day to a day and half to get everything running smoothly.

Then I started finding the problems after I attempted to sync with the iPhone.

I had delegated all of the calendars my wife updates to me — on occasion I do put an entry or two into the master calendar.  I figure that’s all I’ll need to manipulate and see the calendars on my iPhone.  However, when I went into iTunes, I was very surprise to find that none of the delegated calendars showed up as possible sync candidates.  The only iCal related entry was my new iCal server calendar (my local iCal calendars were still showing of course.)  In order to sync the ‘master calendar’ I had to go into my wife’s account and publish the appropriate calendars and then subscribe to them from my iCal application.  That allowed the calendars to be displayed in iTunes and they seem to sync fine with the iPhone after that.  However – this created a mess in my local iCal application because now I had double entries – one for the delegated calendars and the second for the subscribed calendars.  So I have to disable the duplicate calendars from showing.

The next issue I found out about was that the iPhone calendar application will not allow you to edit an existing entry or add a new entry to that particular calendar.  As a matter of fact, the only calendar you can add events to are your local iCal calendars — you can not even manipulate your own iCal Server calendar!

So now I’m totally frustrated.  I can’t stand that I’m this close to have a great solution — but the damn iPhone sync’ing is so immature.  I guess I could have save myself a ton of time by going online and reading about all these issues before I attempted this — as there are a lot of people who have complained about this.  oh well, lesson learned.

Now — I have to find another solution.  Gmail? Zimbra?


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