Hi @Henderson, Ivan (GE Gas Power, consultant)
I deleted the screenshots because it contains some private information.
From the screenshots, I note that you configure two email accounts in one Outlook profile. This issue is caused by that Outlook only display the calendar information for default account. We could change this setting via the followings:
File->Account Settings->Data Files
You could set the email account which calendar you want to display in To-Do-Bar as the default
Then you could see the calendar normally. If it is not update immediately, you could restart Outlook and try again.
If an Answer is helpful, please click "Accept Answer" and upvote it.
Note: Please follow the steps in our documentation to enable e-mail notifications if you want to receive the related email notification for this thread.