Automated random testing is a proven way to identify bugs and precondition violations, and this even in well tested libraries. In the context of statically typed languages, current automated random testing tools heavily take advantage of static method declaration (argument types, thrown exceptions) to constrain input domains while testing and to identify errors. For such reason, automated random testing has not been investigated in the context of dynamically typed languages. In this paper we present the key challenges that have to be addressed to support automated testing in dynamic languages.