A method and system for capturing and annotating measurement data includes communicatively connecting a mobile computing device to one or more measurement devices, and receiving measurement data from the one or more measurement devices. The mobile computing device stores the received measurement data and annotates the stored measurement data with metadata. The metadata includes group identifying information that associates the stored measurement data with other data having similar group identifying information. In at least one embodiment, measurement data is automatically associated with the group identifying information based on the measurement data being captured within a predetermined amount of time of each other or within a predetermined distance of each other as determined by a positioning system. The metadata may include, for example, one or more of a time, a location, a test point, a work order, a task list, a job instruction, a technician identifier, a text note, a voice note, an image, a video, and an image annotation.