only bob can prevent double-sending in this simple example

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Is there a way to prevent this at the wallet to wallet level or only at the mint level?

So that means if alice does send to carol AND Jon, then whoever redeems faster (Alice, Jon) from Bob gets the money?

That’s what I’m thinking, doesn’t sound like a good system

No. That's why when someone preaches to use Cashus offline I laugh. And for online we have LN.