We study a sequential estimation problem for an unknown reward in the presence of a random horizon. The reward takes one of two predetermined values which can be inferred from the drift of a Wiener process, which serves as a signal. The objective is to use the information in the signal to estimate the reward which is made available until a stochastic deadline that depends on its value. The observer must therefore work quickly to determine if the reward is favorable and claim it before the deadline passes. Under general assumptions on the stochastic deadline, we provide a full characterization of the solution that includes an identification with the unique solution to a free-boundary problem. Our analysis derives regularity properties of the solution that imply its ``smooth fit'' with the boundary data, and we show that the free-boundary solves a particular integral equation. The continuity of the free-boundary is also established under additional structural assumptions that lead to its representation in terms of a continuous transformation of a monotone function. We provide illustrations for several examples of interest.