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Hi @delanataylor,
What happens to the stuff they published under their free account?
The Published Posts under the free account will go to draft automatically when you updated the premium role.
After upgrading the premium role, they access all posts, it will not move with them, and No need to repost everything under the new role.
If you downgrade the role from premium to free, then all published posts under the premium account will not accessible.
Still, If you are still having queries, then kindly contact through the website for further assistance.
Hope you understand.