Hi Craig, most likely the issue is that you're using a different account to complete all components of the web course than the one you used to enroll in the learning plan. Even if your accounts are linked, the learning plan will update only if the same account is used to complete the resources it contains. If you've completed the course while you were signed in with the same account you used to enroll in the learning plan, please let me know and our team will investigate.
Also, note that you can complete web course exercises using your ArcGIS trial account without changing the organizational account you're signing in with to work through the web course instructions (open ArcGIS Online in a new, preferably incognito browser window and sign in with your trial account).
