The existence of a security vulnerability in a system does not necessarily mean that it can be exploited. In this research, we introduce Autosploit -- an automated framework for evaluating the exploitability of vulnerabilities. Given a vulnerable environment and relevant exploits, Autosploit will automatically test the exploits on different configurations of the environment in order to identify the specific properties necessary for successful exploitation of the existing vulnerabilities. Since testing all possible system configurations is infeasible, we introduce an efficient approach for testing and searching through all possible configurations of the environment. The efficient testing process implemented by Autosploit is based on two algorithms: generalized binary splitting and Barinel, which are used for noiseless and noisy environments respectively. We implemented the proposed framework and evaluated it using real vulnerabilities. The results show that Autosploit is able to automatically identify the system properties that affect the ability to exploit a vulnerability in both noiseless and noisy environments. These important results can be utilized for more accurate and effective risk assessment.