Safety is often understood as freedom from unacceptable loss; reliability as the capacity to accomplish particular outcomes repeatedly through operational sensitivity. Both compel performance objectives for high-risk organizations. If either is absent, people, organizations, and their external environments are potentially at unnecessary risk. Focused on continuous performance improvement, debriefs are often implemented to achieve safe, reliable outcomes through post-incident discussion. Research has presumed that debriefs allow teams to pursue safety and reliability simultaneously and without contradiction. However, this theoretical assumption has never been assessed according to how a team’s discourse in debriefs leads to these distinct outcomes. This research adopts Craig and Tracy’s (2021) grounded practical theory methodology to analyze talk in post-competition debriefs of stock car racing pit crews. Analysis of participants’ talk, according to problem and technical levels of grounded practical reconstruction, suggests a central dilemma that constrains pit crews’ efforts toward safety and reliability, namely, a contradiction among performance expectations for regulatory adherence and boundary pushing. Results also include several discursive techniques that pit crews employ during debriefs in response to this dilemma. A model of dilemmatic talk of debriefs situates these outcomes, making what is implicit about this practice more explicit.