A proper understanding of agentive modals promises to clarify issues to do with free will, know how, and other philosophically interesting topics. In this paper I identify one constraint on, and one structural feature of, trying-based versions of the conditional analysis of the agentive modals. I suggest that the constraint and structural feature together provide a novel account of why the famous Lehrer-Chisholm objection to conditional analyses of ability modals is so powerful. I argue that Mandelkern et al.’s ‘Agentive Modals’ (...) (Philosophical Review,126/3, 301–343, 2017) conditional analysis of the agentive modals fails to avoid this problem. I also identify two further problems for their account. I close by summarising a number of criteria which any successful semantic analysis of the agentive modals should satisfy. (shrink)