If my experiences, and the experiences of loads of other folks, are any guide, getting the Apple iPad to sync contacts and calendars with Windows systems is a hit and miss affair. In my case, it was always a miss. I was trying to sync my Outlook contacts and calendar to the iPad and it simply did not work at all. I tried all of the suggestions in the Apple knowledgebase article http://support.apple.com/kb/ht1692 and it still did not work.
My setup: WiFi iPad, Win 7 64-bit pro desktop, Outlook 2007, iTunes 9.1.1 r12. Many of the articles I found while Googling this problem suggested that the solution was to sync via Gmail, but I have no desire to have my entire address book and life history “in the cloud”, even temporarily. The other common solution was to allow Exchange Server to handle the sync, but I don’t use Exchange Server.
I did discover a solution. First you should make sure to turn off calendar and contact syncing in iTunes. Then …
- Save contacts as a vcf.
- Email to iPad.
- Open email in iPad and click on the attachment – it will offer to save all of the contacts (341 for me).
- In Outlook left menu bar, right click on Calendar.
- Choose send via email.
- On email that opens, right click on .ics file and save to desktop.
- Trash email. (Even though iPad mail shows a calendar icon for the .ics file, it won’t open .ics files!!!!!)
- Move .ics file to any web server you can.
- In iPad Safari, browse to .ics file and it will import to the calendar.
Note that this is one way syncing, but that is exactly what I wanted. The contact syncing should work for any email client that can export vcf files. I can confirm that it works with Thunderbird. Hope this saves you some frustration.