To enhance our ability to investigate caregiver-child interactions, the contexts supporting those interactions, and the contribution of both to children’s language learning, we developed the “Parent, Infant, Caregiver Computerized Observation of Language Interactions (PICCOLI; Walker, Hart & Hou, 1995) (OSEP). This system was developed in an effort to more efficiently document the language-related interactions that children experience during infancy and up to age three. Observations using the PICCOLI were conducted originally with notebook computers and wireless microphones, permitting simultaneous recording of environmental and interactional variables related to the language opportunities provided to children. The PICCOLI system uses interval time sampling and digitized language recording linked to coded interactional and ecological variables during observations. The PICCOLI system enables the recording of 127 ecological and interactional events along with real-time recording of communication which can then be transcribed and entered into a language analysis system for coding. Sequential, moment-to-moment relationships between caregiver-child interactions and ecological variables along with frequency information are reported in computer-generated reports for individual children and for groups. The PICCOLI system has served as the basis for observation systems used in a number of our subsequent research projects and the software has been updated for use on Windows-based notebook devices.