We study a mathematical model capturing the support/resistance line method (a technique in technical analysis) where the underlying stock price transitions between two states of nature in a path-dependent manner. For optimal stopping problems with respect to a general class of reward functions and dynamics, using probabilistic methods, we show that the value function is $C^1$ and solves a general free boundary problem. Moreover, for a wide range of utilities, we prove that the best time to buy and sell the stock is obtained by solving free boundary problems corresponding to two linked optimal stopping problems. We use this to numerically compute optimal trading strategies for several types of dynamics and varying degrees of relative risk aversion. We then compare the strategies with the standard trading rule to investigate the viability of this form of technical analysis.
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