Methods and systems are provided for associating contextual data with communication sessions, in particular in technical help desk scenarios. A context logger service running on a central server or on an individual computing device is used to create a log of application specific, often ephemeral, contextual data for a plurality of applications running one or more systems that are in communication with the context logger service across one or more networks. When a communication session between an initiating entity and a receiving entity to request assistance regarding a subject application running on one of the systems is initiated, and if the communication session is deemed to be a candidate for the automatic association of such context data, at least a portion of the application specific contextual data contained in the log is associated with the communication session and delivered to the receiving entity. The receiving entity uses the associated application specific contextual data to provide the requested assistance, or otherwise improve the operations at the receiving entity.