Yes, I have set it to all. In the General Options it states the following:
Regarding Registration: Custom Fields do not appear during repeat registration and/or checkout attempts (i.e., they do not appear for any user that is currently logged into the site). Please make sure that you test registration and/or checkout forms while not logged in (i.e., please test as a first-time customer). Existing users, members, customers may update Custom Fields by editing their Profile.
Which in our case, the user already registered as a free member. He decides to upgrade to a paid plan. As soon as they get to the Pro Stripe Form, this field doesn't show up because he is already a registered user.
That is basically the problem I'm having.