In America, you can’t open a bank account without an address. That means that the homeless population can’t open a bank account (not easily, anyway), and therefore can’t get a debit card.
Cashless is a nice idea, but it is extremely prohibitive against the most vulnerable people (which, sadly, might be part of the point).
There’s an old addage when working with any Microsoft product:
“Wait longer”
In other words, your first click was probably doing its thing. You just needed to wait a little longer to see it work.