I had a good time playing a demo of Outer Rim at UK Games Expo. As Han Solo I even got to attempt the Kessel Run! But I was a little puzzled by how it played out. IIRC on arrival at Kessel I had to execute card 46 (I think) which told me to roll two dice and look for a crit. First roll I failed, so I waited for my next turn, then rolled again. Another fail. Waited and rolled and failed again. Waited and rolled and failed again. This was starting to get boring, and felt weird as well. Surely you get one attempt at a job, and if you fail you have to move on and try something else? Our demonstrator seemd to think I was doing it right though. Puzzled.

Yup, that's what the rules say.

From your description, it seems you were Unskilled at Influence, so you only had 23.44% probability to pass this test. Four attempts give you 65.64% chance to pass it.

A character repeatedly failing at a job he's incompetent at? Makes perfect sense to me.