Tony Vargas
Legend
There's the general rule that the player declares actions and the DM determines uncertainty, maybe calls for a check, and narrates the result.You say here that the rule is one roll only unless the DM grants another (much like 1e does it; and my preference). Others are saying the rule is you can keep trying - and thus keep rolling* - until you either succeed or prove the task is beyond you, and that the DM is bound by this (much like 3e's Take-20).
Which is it?
So it's entirely up to the DM how any repeated declaration of the same action (or variations thereupon) might work out.