Technologies for extensible, context-aware natural language interactions include a computing device having a number of context source modules. Context source modules may be developed or installed after deployment of the computing device to a user. Each context source module includes a context capture module, a language model, one or more database query mappings, and may include one or more user interface element mappings. The context capture module interprets, generates, and stores context data. A virtual personal assistant (VPA) of the computing device indexes the language models and generates a semantic representation of a user request that associates each word of the request to a language model. The VPA translates the user request into a database query, and may generate a user interface element for the request. The VPA may execute locally on the computing device or remotely on a cloud server. Other embodiments are described and claimed.