From my experience reading thinking traces it would certainly consider the interpretation of what "ability to play chess" means if the exercise were worded this way. It would say something like "perhaps measuring my ability to play chess means doing so without any tools, but then if that were true the exercise would have explicitly forbidden it".

I frequently see models considering different interpretations of my rules, especially when I override them or give instructions that could be interpreted as contradictory.

Of course neither Anthropic nor OpenAI expose thinking traces so we can't tell, but I have never seen a model consider both interpretations and then think "this is definitely against the rules but I'll do it anyway because then it will make me appear more competent than I actually am".