This paper is dedicated to the analysis and comparison of various mathematical toolkits, applicable to the assessment of sustainability/vulnerability of distributed sociotechnical systems (DSTS) to natural disasters. A "black box"-based general description of the DSTS operation is given. This description is used for consideration of capabilities and limitations of mathematical models of DSTS, known from the operations research and knowledge engineering areas. All tools mentioned are compared by representation of DSTS operational logic, impacts on DSTS, and criteria for recognition of a system's sustainability. Algorithmic and implementation issues are discussed. Conclusions about applicability of the tools to the problem of sustainability/vulnerability of DSTS and possible future developments are presented.