Problem with Catalog Widgets not showing Enrollments - Pod CHU

Summary

New Enrollments not being displayed by the catalog widget, older ones are.

Content

I'm creating new enrollments for ILT Sessions as we have always done and finding that they are not being shown in our catalog widget.

Tried to replicate in Staging where I found the same behavior, however...
If I change the catalog widget Content - Show Selected Categories setting to All Categories, it sees the new enrollment.
If I then return the Show Selected Categories setting to Manually Select Root Categories with the categories I want, the enrollment is still shown.

Back in Production where I tried the above approach, it still would not show the enrollment in the widget.