Code obfuscation is widely used by software developers to protect intellectual property, and malware writers to hamper program analysis. However, there seems to be little work on systematic evaluations of effectiveness of obfuscation techniques against automated program analysis. The result is that we have no methodical way of knowing what kinds of automated analyses an obfuscation method can withstand. This paper addresses the problem of characterizing the resilience of code obfuscation transformations against automated symbolic execution attacks, complementing existing works that measure the potency of obfuscation transformations against human-assisted attacks through user studies. We evaluated our approach over 5000 different C programs, which have each been obfuscated using existing implementations of obfuscation transformations. The results show that many existing obfuscation transformations, such as virtualization, stand little chance of withstanding symbolicexecution based deobfuscation. A crucial and perhaps surprising observation we make is that symbolic-execution based deobfuscators can easily deobfuscate transformations that preserve program semantics. On the other hand, we present new obfuscation transformations that change program behavior in subtle yet acceptable ways, and show that they can render symbolic-execution based deobfuscation analysis ineffective in practice.