What is your estimation based on? My users sign up with my app and at the moment a free subscription is created for them automatically on sign up, and they can

What is your estimation based on? My users sign up with my app and at the moment a free subscription is created for them automatically on sign up, and they can upgrade to a paid plan from within the app. So I would only ask them to pick a plan again once I switch, not to recreate the whole account. Their account plus data etc would stay the same. Do you think it would still be bad to ask them to pick up a plan again, knowing that the previous subscriptions would be cancelled automatically when they resubscribe? Thanks