As software systems become more complex and configurable, failures due to misconfigurations are becoming a critical problem. Such failures often have serious functionality, security and financial consequences. Further, diagnosis and remediation for such failures require reasoning across the software stack and its operating environment, making it difficult and costly. We present a framework and tool called EnCore to automatically detect software misconfigurations. EnCore takes into account two important factors that are unexploited before: the interaction between the configuration settings and the executing environment, as well as the rich correlations between configuration entries. We embrace the emerging trend of viewing systems as data, and exploit this to extract information about the execution environment in which a configuration setting is used. EnCore learns configuration rules from a given set of sample configurations. With training data enriched with the execution context of configurations, EnCore is able to learn a broad set of configuration anomalies that spans the entire system. EnCore is effective in detecting both injected errors and known real-world problems - it finds 37 new misconfigurations in Amazon EC2 public images and 24 new configuration problems in a commercial private cloud. By systematically exploiting environment information and by learning correlation rules across multiple configuration settings, EnCore detects 1.6x to 3.5x more misconfiguration anomalies than previous approaches.