In the literature on optimal stopping, the problem of maximizing the expected discounted reward over all stopping times has been explicitly solved for some special reward functions (including (x+)ν, (ex − K)+, (K − e− x)+, x ∈ ℝ, ν ∈ (0, ∞), and K > 0) under general random walks in discrete time and Lévy processes in continuous time (subject to mild integrability conditions). All such reward functions are continuous, increasing, and logconcave while the corresponding optimal stopping times are of threshold type (i.e. the solutions are one-sided). In this paper we show that all optimal stopping problems with increasing, logconcave, and right-continuous reward functions admit one-sided solutions for general random walks and Lévy processes, thereby generalizing the aforementioned results. We also investigate in detail the principle of smooth fit for Lévy processes when the reward function is increasing and logconcave.

Consider a geometric Brownian motion Xt(ω) with drift. Suppose that there is an independent source that sends signals at random times τ1 < τ2 < ⋯. Upon receiving each signal, a decision has to be made as to whether to stop or to continue. Stopping at time τ will bring a reward Sτ, where St = max(max0≤u≤tXu, s) for some constant s ≥ X0. The objective is to choose an optimal stopping time to maximize the discounted expected reward E[e−rτiSτi | X0 = x, S0 = s], where r is a discount factor. This problem can be viewed as a randomized version of the Bermudan look-back option pricing problem. In this paper, we derive explicit solutions to this optimal stopping problem, assuming that signal arrival is a Poisson process with parameter λ. Optimal stopping rules are differentiated by the frequency of the signal process. Specifically, there exists a threshold λ* such that if λ>λ*, the optimal stopping problem is solved via the standard formulation of a ‘free boundary’ problem and the optimal stopping time τ* is governed by a threshold a* such that τ* = inf{τn: Xτn≤a*Sτn}. If λ≤λ* then it is optimal to stop immediately a signal is received, i.e. at τ* = τ1. Mathematically, it is intriguing that a smooth fit is critical in the former case while irrelevant in the latter.