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It's common practice to require the signed copy of release before giving the cash of the settlement. The settlement agreement is a binding agreement in any event...so if they don't produce the cash, you then can sue them for breach of contract of the settlement agreement.
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No it wouldn't be unorthodox...tell the attorney you want a signed copy (signed by their client) of the agreement and when you sign it you'll hand deliver it to them with a signed dismissal and expect the check in exchange.
With prejudice would not prevent you from filing a claim over non-payment of the settlement amount because he settlement is a contract, seperae from the underlying action. Hope this answers your questions. Thanks.