ABSTRACT. Attack trees are a well-recognized formalism for security modeling and analysis, but in this work we tackle a problem that has not yet been addressed by the security or formal methods community – namely guided design of attack trees. The objective of the framework presented in this paper is to support a security expert in the process of designing a pertinent attack tree for a given system. In contrast to most of existing approaches for attack trees, our framework contains an explicit model of the real system to be analyzed, formalized as a transition system that may contain quantitative information. The leaves of our attack trees are labeled with reachability goals in the transition system and the attack tree semantics is expressed in terms of traces of the system. The main novelty of the proposed framework is that we start with an attack tree which is not fully refined and by exhibiting paths in the system that are optimal with respect to the quantitative information, we are able to suggest to the security expert which parts of the tree contribute to optimal attacks and should therefore be developed further. Such useful parts of the tree are determined by solving a satisfiability problem in propositional logic.