What's up with Outlook 2003, Outlook 2007 works fine?
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Outlook 2007 and its later versions work fine with dotCal and other CalDav compliant systems like this.
Outllook 2003 is simply not a “modern” calendar sharing program and we would prefer you not use it with this application beta. Most calendar programs today support “1 click” calendar subscription. Outlook 2003 simply does not.
Outlook 2003 does support “Importing” an .ics file by using the Outlook 2003 function “File” > “Import” > “Import an iCalendar File”, and with this function the .ics must also be an older 1.0 iCalender version. The rest of the world is now on iCalendar 2.0.
So we are working on some work arounds, including an Outlook 2003 add, but the good news is the more time that goes by, the less important Outlook 2003 will become.