The notion of timeout (namely, the maximal time to wait before retrying an action) turns up in many networking contexts, such as packet transmission, connection establishment, etc. Usage of timeouts is encountered especially in large-scale networks, where negative acknowledgments (NACKs) on failures have significantly higher delays than positive acknowledgments (ACKs) and frequently are not employed at all. Selection of a proper timeout involves a tradeoff between waiting too long and loading the network needlessly by waiting too little. The common approach is to set the timeout to a large value, such that, unless the action fails, it is acknowledged within the timeout duration with a high probability. This approach is conservative and leads to overly long, far from optimal, timeouts. We take a quantitative approach with the purpose of computing and studying the optimal timeout strategy. The above tradeoff is modeled by introducing a "cost" per unit time (until success) and a...