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I must be missing something - why not just hash all the plaintext passwords, store the hases on the new version of your site, and have it so when users login to the new site it does the right thing.

Why should the users have to know anything?

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Because the original subscription was for 39.00 for a year, and some users might have done this a year ago. It would be nice for them to log in, check out the new platform, see how much uber awesomesauce it has, and then realise that if they get asked to renew again, that their new price of free, is definately worth relisting.

It's just important to not lose any of the new users which this industry has a high churn rate (and we are providing the new service that they have previously been paying for for free, but we have a lot of upsells)

Maybe I'm misunderstanding, but could you not just email the customers and tell them how much better the service is now? and hash the passwords as suggested

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