Hi @Jon Dalrymple and others,
This issue will be fixed in an update today 184.108.40.206, and I take on board what @Samuel and @Creatura said. A UX update here will definitely make the plugin better. Pending some bug fixes, I will make this one a priority. Thanks for the feedback.
Could you please check the customer ID in the Stripe dashboard and confirm that they have a valid credit card on file?
I'm trying to find out for you why the subscription got cancelled. Thanks for allowing support access.