Edit both plans and ensure "Propose plan for upgrades only if it is more expensive" under the Workflows tab is set to "No: It will be possible to upgrade to this plan (for free with pro-rating) if all conditions below and elsewhere are met". This won't have any impact on existing subscriptions though and will only impact new subscribers so that maybe why you're still having this issue since existing subscriptions will have already been put into an "upgraded to" state.
Kyle (Krileon) Community Builder Team Member Before posting on forums:
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krileon
