Why are Course Level Assignments via Required Initiative not Allowing Offering Enrollments?

Summary:

I am an admin and learner in our system. We recently received an issue from an employee stating they see the following message when clicking their assignment: "There are no offerings available at this time. Check back later."

I was able to recreate this issue using the following path: My Client Groups>Learning>Course>Learners>Learning Initiative>Required Initiative>*Enter details* Must re-take Learning is default>Submit. I then navigate the following Me>Learning>Find course level enrollment>Photo Provided below.

I have confirmed the following before submitting this question:

>All default settings are set to "Detail View" for the course and offerings