The web information behaviors of users as they interacted with a metadata navigator, the Personal Information (PI) Agent, and reflected upon their interaction experiences were studied. The process included studying the complete iterative (repeated) cycle of information needs, information seeking, and information use of users interacting with an internet-based prototype metadata PI Agent tool. Detlor’s theory of web information behaviors of organizational users was utilized as a theoretical foundation for studying human-information interactions via the PI Agent tool. The qualitative research design allowed for the use of triangulation within the context of a one-group pretest-posttest design. Triangulation occurred in three phases: (a) observe, (b) collect, and (c) reflect. Observations were made as participants solved three problem situations. Participants’ computer log and print screen data were collected, and follow-up interviews were conducted once all posttest sessions ended to enable users to reflect on their experiences. The three triangulation phases ensured saturation of data and greater depth regarding the participants’ information behaviors. Content analysis occurred via exploratory pattern analysis using the posttest Problem Steps Recorder (PSR) log data and on the six interviewees’ follow-up interview data. Users engaged in iterative cycles of information needs, information seeking, and information use to resolve the presented problem situations. The participants utilized the PI Agent tool iteratively to eliminate their knowledge gaps regarding the presented problem situations. This study was the first to use PSR log data for capturing evidence of the iterative search process as defined by Detlor. The implications for best practices were inspired by participant feedback, and recommendations for further study are made.