We consider a class of optimal stopping problems where the ability to stop depends on an exogenous Poisson signal process - we can only stop at the Poisson jump times. Even though the time variable in these problems has a discrete aspect, a variational inequality can be obtained by considering an underlying continuous-time structure. Depending on whether stopping is allowed at t = 0, the value function exhibits different properties across the optimal exercise boundary. Indeed, the value function is only 𝒞 0 across the optimal boundary when stopping is allowed at t = 0 and 𝒞 2 otherwise, both contradicting the usual 𝒞 1 smoothness that is necessary and sufficient for the application of the principle of smooth fit. Also discussed is an equivalent stochastic control formulation for these stopping problems. Finally, we derive the asymptotic behaviour of the value functions and optimal exercise boundaries as the intensity of the Poisson process goes to infinity or, roughly speaking, as the problems converge to the classical continuous-time optimal stopping problems.