The Calendar Checking Tool for Outlook (CalCheck) is a command-line program that checks Microsoft Outlook Calendars for problems. The tool opens an Outlook profile to access the Outlook Calendar. It performs various checks, such as permissions, free/busy publishing, delegate configuration, and automatic booking. Then each item in the calendar folder is checked for known problems that can cause unexpected behavior, such as meetings that appear to be missing. As CalCheck goes through this process, it generates a report that can be used to help diagnose problem items or identify trends.