Scenario:
User books a Time Off for Monday, Tuesday and Wednesday in Web TimeSheet. He then synchronizes the Web TimeSheet calender with iCal so that the Time Off information can be viewed in iCal. It provides the data to be viewed in 3 formats as follows,

  • View by week
  • View by Month
  • View by day

If the time off booking is viewed in iCal calendar in View by Weekformat, the booking is displayed correctly on all three days. Similarly, in the View by Day, proper information can be viewed. However, in the View by Month, it only lists Monday as the day off and the other two days does not get highlighted. Moreover, if we book a partial time off on Monday and a full time off for Tuesday and Wednesday and then sync it with iCal, the iCal calender will show a time off booked only on Tuesday in View by Month.

Resolution:
This is identified as a bug in iCal. The iCal View by Month is designed to show only day spanning events. Here is an example of others running into similar issues and hence they sync their iCal with Google Calendar,

https://discussions.apple.com/thread/7643050