Cyber security is a domain for which researchers have struggled to understand the boundaries, scope, and limitations. The cyberspace environment involves very large numbers of possible states, includes data from multiple abstraction layers (sometimes simultaneously), and contains physical and non-physical entities, all of which are dynamic, complex, interactive, and context dependent. Successful approaches to solving problems in cyber security and cyber data analysis tend to be exploratory or learning-based because the foundational elements and technologies change rapidly. Additionally, since cyberspace is fundamentally an adversarial domain, cyber security problems are often human-centered and exist in a social context. The 2014 International Workshop on Human-Machine Teaming in Cyber (HMTC 2014) is focused on exploring the issues related to how humans and agents work in cyber security and cyber data analysis, and how that work is facilitated through automation.