Abstract: We consider a discounted infinite horizon optimal stopping problem. If the underlying distribution is known a priori, the solution of this problem is obtained via dynamic programming (DP) and is given by a well known threshold rule. When information on this distribution is lacking, a natural (though naive) approach is ``explore-then-exploit," whereby the unknown distribution or its parameters are estimated over an initial exploration phase, and this estimate is then used in the DP to determine actions over the residual exploitation phase. We show: (i) with proper tuning, this approach leads to performance comparable to the full information DP solution; and (ii) despite common wisdom on the sensitivity of such ``plug in" approaches in DP due to propagation of estimation errors, a surprisingly ``short" (logarithmic in the horizon) exploration horizon suffices to obtain said performance. In cases where the underlying distribution is heavy-tailed, these observations are even more pronounced: a single sample exploration phase suffices.