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A New Addition to the Family

Google Calendar, Plaxo, Outlook, and the iPhone - How to Sync Multiple Calendars

A couple of weeks ago I got an iPhone and have been trying to figure out the optimal way to get it synchronized with all of my contacts, calendars, and tasks ever since.  I use the following services:

  • Google Calendar (work calendar via Google Apps)
  • Microsoft Outlook (currently my master calendar and currently sync'd with my Google Calendar)
  • Plaxo (to sync my calendar and contacts)
  • Remember the Milk (tasks)

What I'd like to have is:

  • Google Calendar 1 (Work Calendar)
  • Google Calendar 2 (Personal Calendar)
  • Plaxo (Contacts)
  • Remember the Milk (Tasks)
  • Access to all of the above via separate calendars in Outlook
  • iPhone (Over the Air access to all calendars, contacts, and tasks)

I've spent more time than I care to admit trying to figure out how to get all of my info sync'd.  It looks like there is no one solution (not sure about MobileMe btw... I can't figure out if it can sync with Google Calendar) that can help me get two way synchronization working between all of these various services.  However, after a significant amount of pulling of hair and gnashing of teeth I think I've come up with an (almost) workable solution for my contacts and calendars.

I should mention before we get started that Remember the Milk (RTM) had a handy iPhone enabled web interface so I'll leave that out of the equation for now. Also, I could view my Plaxo and Google Calendars directly via my iPhone browser, but then I would be missing out on getting pop up notifications from my calendars on my phone. 

The trick to getting all of my calendars sync'd to one common location is that Plaxo can synchronize all of my calendars to Outlook.  Outlook can then sync to my iPhone.  So, I'm missing the OTA aspect but everything else will be in sync (and I can keep my work and personal calendars separate).  Nirvana!  Except for a couple of things...

Step 1 - Sync Google and Plaxo making sure to tell Plaxo to keep my Google Work Calendar in a separate folder... Life is good, two-way sync works... almost.  Some of my recurring appointments refuse to sync between Google and Plaxo.  The common threads seem to be that each is a recurring appointment I've been invited to by someone else.  I've got a ticket open with Plaxo on this. 

Step 2 - Sync Plaxo with Outlook... As always, this works like a charm. 

Step 3 - Sync Outlook with my iPhone... My default Outlook calendar syncs just fine, but the folder configured to sync with my work calendar doesn't show up either in iTunes or my iPhone.  Crap.  I tried several things to get my work calendar folder to sync with my phone to no avail until I noticed that my work calendar folder in Outlook was a sibling in the folder hierarchy to my default calendar.  I right clicked on the calendar and selected 'Move "Work Calendar" to...', then selected my "Calendar" and clicked "Ok".

At this point my "Work Calendar" showed up in my Outlook 2007 folder hierarchy as being a child of my default "Calendar".  I then sync'd my iPhone with Outlook using iTunes and voila - both my default "Calendar" and my separate "Work Calendar" appeared on my phone!