Hi, @seconndivers ! Welcome to the Square Community!
Here’s a breakdown of what Square can and can’t do right now — and when you might need an add-on (or workaround) to get what you want.
What you can do already with Square: digital forms & contracts
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Square supports digital forms / agreements (called Square Contracts) that you can create and send to customers. These allow for electronic signing.
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If you use Square Appointments (Plus or Premium) and your customer books a service, you can set it up so a “contract / form” is automatically sent to them after booking. That helps capture waivers, intake info, or forms needing signatures.
However: these automated forms are tied to appointments,not purchases of “products.”
What Square currently does not support
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There’s no built-in feature in Square that automatically emails a fillable PDF after a product purchase.
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The “automation on purchase → send form” workflow only works for services/appointments (via Square Contracts), not standard online store purchases/items
So if your “membership option” is set up as a product, Square won’t trigger a contract or form automatically when someone buys it, at least with built-in Square tools.
What you can do instead,using add-ons or manual workarounds
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Use a 3rd-party form tool like Jotform, Paperform, or similar. After purchase you can manually send them a link to the form to fill out and sign. Many sellers do this when using Square + extra paperwork for memberships/services
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If you use appointments instead of a “product,” switch your membership offer to a “service.” Then enable Square Contracts to auto-send a form when that “service” is booked.
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Alternatively, after a product sale, manually send the form (via email) using Square Messages or your own email, though this is manual, it works reliably.
I hope this provides some clarity!
