Lassooing users and putting them down to monkey around with your application may be the best way to spot deficiencies in your freshly baked program.
But it is also where some jaw-dropping things occur. Stuff you really did not expect to happen, made you facepalm for your own stupidity or the users, let us in on the fun!
My story is not one of real stupidity, but just sheer disbelief:
I developed a simple game for elderly to gradually become acquainted with a mouse, from previous users it was obvious that we needed to be clearer about that the buttons of the mouse did not need to be pressed to move the cursor, no harm no foul.
However the next user came in, sat down and got straight into it of course pressing the buttons while moving and generally having a good time. But then in the next level, 'clicking', nothing worked, he did everthing properly, I took over to try myself...nothing. No click was registering, very weird, it worked ok with everyone else.
Luckily it was the last user, and time was up. So I went home to take a look at what was wrong. Turns out the program was absolutely fine... But the man, a welder his whole life with all his strength still there, had totally crushed the internals of the mouse in the first levels...I binned the mouse with a big grin on my face.
Needless to say, I did not see that one coming...