Hey, thanks for the question. I’ll answer point by point, based on what’s already been publicly confirmed.
What definitely triggers the move to the new usage-based pricing, and it’s irreversible so you can’t go back to legacy:
Upgrading to Pro+ or Ultra
Changing your billing cycle monthly ↔ annual via the new checkout
Cancelling and subscribing again
The opt-out option that used to let you stay on legacy isn’t available anymore, it was turned off. So once you leave legacy, there’s no way back.
About renewal annual vs monthly. There’s no special mechanical difference in how they’re processed. But I don’t want to give a hard guarantee about what happens on a clean renewal of the same plan, since legacy plan policy can change and I can’t promise legacy pricing will stay forever. Always double-check the current terms at Cursor · Pricing.
A couple practical notes about legacy while you’re still on it: