I use Outlook at work on a PC using the Windows version of iTunes to sync my iPhone. I only sync my calendar and contacts. Nothing else. At home, I sync the same iPhone on a Mac using iTunes for everything else except calendar and contacts. It works, but I would like to use the iPhone as a conduit to sync calendars and contacts on both machines. iCal and Address book on the Mac and Outlook on the PC. Every time I try it, it doesn’t work and it makes a mess of my files. Can this be done, or is it hopeless?
— Robert
I'd stop trying to use your iPhone as a conduit between Outlook and iCal/Address Book and instead look at how you can sync your PC and Mac. There should be a solution or two for that. The idea is to keep all three in sync, so it doesn't necessarily matter which talks to which as long as all three get the same data eventually.
I would certainly like to sync my PC at work and my Mac at home, but I don't think there is much chance of that. IT department tightly controls the network. Truth is they were less than enthusiastic about letting my sync my iPhone using a local copy of iTunes on my desk computer. That's why I was trying to use the iPhone as a conduit. At this point, that means Outlook on the PC and my iPhone are synced for Calendar and Contacts; my Mac is not synced for Calendar and Contacts (which means I just don't use it). Any ideas? By the by, just bought your book. Great job!
It sounds like your work computer is your main place for calendar and contacts, so it has to start there. And if your IT dept has it locked down, then it is up to them what you can do. Can you sync it to a system online -- like Google Calendar/Contacts? Then you can sync your Mac to that.
I'm not a Windows Outlook user, as you might expect, so there's not too much I can suggest.