What is needed, from a technical standpoint, to make this happen?

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Technically it's already possible, many websites already implement it.

The problem is majority of internet users don't have Bitcoin or a lightning wallet.

And because of that, the majority of websites arent using paywalls.

So from a social/behavior standpoint, I suppose something like a browser extension wallet that could be easily topped up and seamlessly send sats as sites are accessed?

For most users, custodial is easier. Then fiat to sat conversions like #[4]​ is doing. Maybe?