Behavior-based analysis of dynamically executed binaries has become a widely used technique for the identification of suspected malware. Most solutions rely on function call patterns to determine whether a sample is exhibiting malicious behavior. These system and API calls are usually regarded individually and do not consider contextual information or process inter-dependencies. In addition, the patterns are often fixed in nature and do not adapt to changing circumstances on the system environment level. To address these shortcomings, this paper proposes a sentiment extraction and scoring system capable of learning the maliciousness inherent to n-grams of kernel events captured by a real-time monitoring agent. The approach is based on calculating the log likelihood ratio (LLR) of all identified n-grams, effectively determining neighboring sequences as well as assessing whether certain event combinations incline towards the benign or malicious. The extraction component automatically compiles a WordNet-like sentiment dictionary of events, which is subsequently used to score unknown traces of either individual processes, or a session in its entirety. The system was evaluated using a large set of real-world event traces collected on live corporate workstations as well as raw API call traces created in a dedicated malware analysis environment. While applicable to both scenarios, the introduced solution performed best for our abstracted kernel events, generating both new insight into malware–system interaction and assisting with the scoring of hitherto unknown application behavior.