"What would you roll for that?"

How I’d rule those ones, off the top of my head:

Playing chess, 3D or otherwise, could easily be done in a number of ways, with different players favouring different approaches. Reason is probably the best attribute, as it covers logic and the like, but either Daring (for bold ploys and cunning gambits) or Insight (for judging your opponent and trying to predict what they’ll do) might work too. Command and Security both contain elements of strategy and tactics, so either of those work nicely, but Science (covering puzzles, analysis, and similar) works too. I imagine that Spock favoured a Reason + Science approach, while Kirk may be more Daring + Command.

Holoprogramming would commonly be Control + Engineering - a mixture of precision and technical knowledge - but a lot of holodeck technology seems fairly intuitive, so I imagine that you might substitute a different Discipline depending on what you’re trying to simulate. A combat simulation might use Security, experimental computations (using the holodeck to simulate a dangerous experiment) might use Science, medical or therapeutic holography might use Medicine.

Recalling trivia is likely to rely on Insight or Reason (instincts or logic), but the Discipline is likely to be whatever feels right at the time, or the context of the situation.

Holding your drink… that’s Fitness, and then either Security (as a general “tough guy” Discipline) or Medicine (for knowing how it affects the body and acting accordingly).

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