A couple of nights ago I spent an hour cleaning up what I initially alleged to be a problem with Google’s calendaring servers, but which closer examination revealed to be a case of user error. And I must reluctantly admit that user was me: in my infinite enthusiasm for all available technologies, not to mention the recent need to reinstall the software on both my iPad and iPhone, I somehow detonated an excessive number of syncing systems.

Three, to be precise. That’s right: I had Google Sync Services, MobileMe and BusySync all merrily running on my computer, trying to keep my various calendars harmonized. With all those services running simultaneously, it’s amazing that my biggest problem was missing a few calendar events: I would have expected to rip a hole in the space-time continuum.

Meanwhile, my iPad was set to sync with Google, and my iPhone was set to sync with nothing at all — or rather, nothing cloud-based. So I guess that explains why events I added to my iPhone never showed up on my Google calendar or desktop: it’s kind of tough to make syncing work when you’re relying on the bi-monthly event in which I physically connect my iPhone to my computer.

So in the interest of preventing future mishaps (which will likely be precipitated by future upgrades), I want to capture the lessons of my recent misadventures. These really belong in the category of “notes to self”, but then again, so does a lot of my documentation. The main reason I blog it is because I figure while I’m helping myself, I might as well try to be useful to others.

Current setup:

  • On my Macbook: iCal is set to sync via Google CalDav (selected in iCal preferences/Accounts). MobileMe is disabled in iCal Accounts. I have thinned iCal to a single calendar (my awsamuel Google calendar) in the hopes this will prevent confusion, but let’s be realistic: I’ll subscribe to more calendars over time, and probably create multiple calendars of my own. BusySync is still installed but is not running (I will double-check that it is still not running next time I reboot, in case it’s set to turn on at startup, but I don’t think it is.)
  • On my iPhone: Calendar syncing is currently turned off while I see if this new setup is working. Once I’m sure the Macbook-Google sync is going well, I’ll turn syncing back on by following Google’s instructions.
  • On my iPad: Calendar syncing is currently turned off while I see if this new setup is working. Once things are working smoothly between the Macbook, Google and the iPhone, I’ll follow the same iPad setup I use on the iPhone.

Notes and vulnerabilities:

  • Fewer calendars more better: I want to avoid the proliferation of calendars that happened in iCal. If I add more calendars in the future I want to add them from within Google rather than from within iCal, so I don’t end up with multiple sets of calendars (worse case seems to be three sets: On My Mac, MobileMe and Google). Ideally I will keep subscribe-only calendars (e.g. Rob’s, and other colleagues) separate from my own read/write calendars.
  • MobileMe calendaring upgrade: The new version of MobileMe changed how BusySync works, which may have been when things started to go sidewise. I need to keep an eye on what happens when iCloud comes along; if it adds syncing services to the current setup I could end up with another nightmarish dual-sync scenario.
  • Software reinstalls: Upgrading to Lion, restoring my iPad and restoring my iPhone are all moments when my calendaring could have gone off-track. Likewise when I introduced my shared Emily Carr calendar into the mix (necessary to fit with Emily Carr’s scheduling system). In future I want to double-check all my syncing setups after any major upgrade (i.e. look at account and syncing settings on the Macbook, iPhone and iPad).
  • Delegation: I don’t really understand what the “delegation” settings are for in iCal, which makes me nervous. I’ve got to dig around and find out how these should be set up so that I don’t accidentally publish my electrolysis appointments to Facebook. Also, I should really make some electrolysis appointments.

    Delegation settings window shows list of accounts with checkboxes

    Delegation settings in iCal

  • Emily Carr syncing: Speaking of Emily Carr, I still don’t feel like I’ve got the right structural relationship between my Google calendar and my Emily Carr calendar. I need to figure out which direction I want the sharing to work and which account should write to which calendar. This may require installing a new brain.
  • Tungle.me: I’m curious about trying Tungle as a way of making some of my scheduling back-and-forths a bit easier. Again, this will introduce a wrinkle into my sync-a-thon so I will want to check everything over again once I see how it’s working.
  • Morgan: The current wetware alternative to Tungle is one Morgan Brayton, who actually has to deal with the insanity of keeping my schedule vaguely in order. We need to make sure that nothing I’ve done has altered her access to my calendar, since any limits on her access will indeed bring this whole show to a grinding halt.

Of course, it’s possible that I’ve messed something up along the way, thereby deleting items from my calendar. So if you have a meeting scheduled with me in the next few weeks and I don’t show up, that’s why. In fact, this sounds like such a useful excuse that I think I will henceforth write monthly blog posts about my calendar tweaking, and accompany each one with a blanket disclaimer.