In mathematics, the theory of optimal stopping is concerned with the problem of choosing a time to take a particular action, in order to maximise an expected reward or minimise an expected cost. Optimal stopping problems can be found in areas of statistics, economics, and mathematical finance (related to the pricing of American options). A key example of an optimal stopping problem is the secretary problem. Optimal stopping problems can often be written in the form of a Bellman equation, and are therefore often solved using dynamic programming.
Discrete time case
Stopping rule problems are associated with two objects:
- A sequence of random variables , whose joint distribution is something assumed to be known
- A sequence of 'reward' functions which depend on the observed values of the random variables in 1.:
Given those objects, the problem is as follows:
- You are observing the sequence of random variables, and at each step , you can choose to either stop observing or continue
- If you stop observing at step , you will receive reward
- You want to choose a stopping rule to maximise your expected reward (or equivalently, minimise your expected loss)
Continuous time case
Given a gain processes defined on a filtered probability space and assume that is adapted to the filtration. The optimal stopping problem is to find the stopping time which maximizes the expected gain
where is called the value function. Here can take value .
A more specific formulation is as follows. We consider an adapted strong Markov process defined on a filtered probability space where denotes the probability measure where the stochastic process starts from . Given continuous functions , the optimal stopping problem is
This is sometimes called the MLS (which stand for Mayer, Lagrange, and supremum, respectively) formulation. 
There are generally two approaches of solving optimal stopping problems.  When the underlying process (or the gain process) is described by its unconditional finite dimensional distributions, the appropriate techniques of solution are based on concepts and methods from martingale theories, and is therefore called the martingale approach, the most important concept of which being Snell envelope. In the discrete time case, if the planning horizon is finite, the problem can also be easily solved by dynamic programming.
When the underlying process is determined by a family of (conditional) transition functions leading to a Markovian family of transition probabilities, very powerful analytical tools provided by the theory of Markov processes can often be utilized and this approach is referred to as the Markovian method. The solution is usually obtained by solving the associated free-boundary problems (Stefan problems).
A jump diffusion result
where is an -dimensional Brownian motion, is an -dimensional compensated Poisson random measure, , , are given functions such that a unique solution exists. Let be an open set (the solvency region) and
be the bankruptcy time. The optimal stopping problem is:
It turns out that under some regularity conditions,  the following verification theorem holds:
If function satisfies
- where the continuation region
- on , where is the infinitesimal generator of
Then for all . Moreover, if
Then for all and is an optimal stopping time.
These conditions can also be written is a more compact form (integro-variational inequality):
Coin tossing ( converges)
You have a fair coin and are repeatedly tossing it. Each time, before it is tossed, you can choose to stop tossing it and get paid (in dollars, say) the average number of heads observed.
You wish to maximise the amount you get paid by choosing a stopping rule. If Xi (for i ≥ 1) forms a sequence of independent, identically distributed random variables with Bernoulli distribution
then the sequences , and are the objects associated with this problem.
House selling ( does not necessarily converge)
You have a house and wish to sell it. Each day you are offered for your house, and pay to continue advertising it. If you sell your house on day , you will earn , where .
You wish to maximise the amount you earn by choosing a stopping rule.
In this example, the sequence () is the sequence of offers for your house, and the sequence of reward functions is how much you will earn.
Secretary problem ( is a finite sequence)
You are observing a sequence of objects which can be ranked from best to worst. You wish to choose a stopping rule which maximises your chance of picking the best object.
Here, if (n is some large number, perhaps) are the ranks of the objects, and is the chance you pick the best object if you stop intentionally rejecting objects at step i, then and are the sequences associated with this problem. This problem was solved in the early 1960s by several people. An elegant solution to the secretary problem and several modifications of this problem is provided by the more recent odds algorithm of optimal stopping (Bruss algorithm).
Economists have studied a number of optimal stopping problems similar to the 'secretary problem', and typically call this type of analysis 'search theory'. Search theory has especially focused on a worker's search for a high-wage job, or a consumer's search for a low-priced good.
The holder of an American option is allowed to exercise the right to buy (or sell) the underlying asset at any time before or at the expiry date. Therefore the valuation of American options is essentially an optimal stopping problem. In a classical Black-Scholes set-up, let be the risk-free interest rate, and be the dividend rate and volatility of the stock. The stock price follows geometric Brownian motion
under the risk-neutral measure. When the option is perpetual, the optimal stopping problem writes
where the payoff function for call option and for put option. The variational inequality is
where is the exercise boundary. The solution of it is known to be 
- (Perpetual call) where
- (Perpetual put) where
If the expiry date is finite, the problem is associated with a 2-dimensional free-boundary problem with no known closed-form solution.
- Peskir, Goran; Shiryaev, Albert (2006). Optimal Stopping and Free-Boundary Problems. Berlin: Birkhäuser Basel. ISBN 3764324198.
- Øksendal, Bernt; Sulem, Agnès (2007). Applied Stochastic Control of Jump Diffusions. Berlin: Springer. ISBN 3540698256.
- Karatzas, Ioannis; Shreve, Steven (1998). Methods of Mathematical Finance. New York: Springer. ISBN 0387948392.
- T. P. Hill. "Knowing When to Stop". American Scientist, Vol. 97, 126-133 (2009). (For French translation, see cover story in the July issue of Pour la Science (2009))
- Optimal Stopping and Applications, retrieved on 21 June 2007
- Thomas S. Ferguson. "Who solved the secretary problem?" Statistical Science, Vol. 4.,282-296, (1989)
- F. Thomas Bruss. "Sum the odds to one and stop." Annals of Probability, Vol. 28, 1384–1391,(2000)
- F. Thomas Bruss. "The art of a right decision: Why decision makers want to know the odds-algorithm." Newsletter of the European Mathematical Society, Issue 62, 14-20, (2006)
- R. Rogerson, R. Shimer, and R. Wright (2005), 'Search-theoretic models of the labor market: a survey'. Journal of Economic Literature 43, pp. 959–88.