Code obfuscations are semantics-preserving code transformations used to protect a program from reverse engineering. There is generally no expectation of complete, long-term, protection. Rather, there is a trade-off between the protection afforded by an obfuscation (i.e. the amount of resources an adversary has to expend to overcome the layer of confusion added by the transformation) and the resulting performance overhead. In this paper we examine the problems that arise when constructing an Obfuscation Executive. This is the main loop in charge of a) selecting the part of the application to be obfuscated next, b) choosing the best transformation to apply to this part, c) evaluating how much confusion and overhead has been added to the application, and d) deciding when the obfuscation process should terminate.