Hussar
Legend
/snip
In order for there to be a check, there would have to be a meaningful consequence for failure. Reasonable people can disagree on what constitutes "meaningful" and only the context of playing the game will really tell. But in this example, the players don't seem to think there is a consequence for failing this action (since it's no bigs to just pile on), so maybe there shouldn't have been a roll to begin with - they just succeed or fail outright. If there is a consequence and they're willing to keep incurring it, then fair enough, that's on them.
/snip
Just because I so rarely get to do this, I agree 100% with Iserith here. We might disagree on some points, but, here is one where I am in complete agreement. There's no consequences, just get on with it. I recently was playing in a game where the DM insisted we keep rolling and it just made me completely check out of the scene immediately. I knew there were no consequences to what I was doing and we had all the time in the world to do it and I knew that my character was actually capable of doing it. Don't bother rolling.