We have multiple tools to help you automatically diagnose an issue, troubleshoot, and fix problems with Outlook.
Classic Outlook troubleshooters
Note: Classic Outlook troubleshooters are not applicable to new Outlook for Windows. Check to see if the new Outlook toggle is turned on or off. If it's on, please go to Troubleshooting Outlook issues.
Get Help has troubleshooters for classic Outlook for Windows you can run for many common scenarios, such as Outlook startup or profile setup problems. These often help resolve issues without the need to contact support.
For more information and steps to install these troubleshooters, see: Classic Outlook troubleshooters.
Calendar Checking Tool for Outlook (CalCheck)
CalCheck is a program that checks your Outlook calendar for problems, and performs various checks on general settings, such as permissions, free/busy publishing, delegate configuration, and automatic booking. Then, each item in your calendar folder is checked for known problems that can cause unexpected behavior, such as meetings that seem to be missing.
For more information and to install the tool, please visit: Calendar Checking Tool for Outlook (CalCheck).