Scheduling and managing events using Outlook.com calendar
Hi Craig Ruane,
Thanks for the information. As I understand, events you have added on your MS Office Outlook is not syncing to your Outlook.com Calendar.
As initial troubleshooting, please try removing and re-adding your Outlook.com in MS Office Outlook. You may refer to this article for steps on how to do this: Add Outlook.com to Outlook
Also, make sure that you have the latest version of Outlook Hotmail Connector.
Let us know how things turn out.
Thank you.