This research examines the relationship between anticipatory pushing of information and trust in human– autonomy teaming in a remotely piloted aircraft system - synthetic task environment. Two participants and one AI teammate emulated by a confederate executed a series of missions under routine and degraded conditions. We addressed the following questions: (1) How do anticipatory pushing of information and trust change from human to human and human to autonomous team members across the two sessions? and (2) How is anticipatory pushing of information associated with the trust placed in a teammate across the two sessions? This study demonstrated two main findings: (1) anticipatory pushing of information and trust differed between human-human and human-AI dyads, and (2) anticipatory pushing of information and trust scores increased among human-human dyads under degraded conditions but decreased in human-AI dyads.