endless enroll loop

I have users enrolling in a free course. When they come back, login and try to load the course, it tells them that they need to enroll (but they already did). If the user tries to enroll again, it tells them that they are already enrolled, creating an endless loop.
If I refresh the page, it correctly states they can begin to take the course.

Any ideas (obviously I can’t ask user to refresh the page every time) ? When I added the login/logout to the menu, and when I am on the course page (logged in and enrolled) and incorrectly shows that I need to enroll, I see Login in the menu. When I refresh the page, I see a Logout in the menu. Something wrong with sessions/cookies? I tried this in incognito and also with users who are there for the first time and they are experiencing the same issues.

Any pointers would be appreciated. Thanks