Modern safety-critical systems, such as aircraft and spacecraft, crucially depend on rigorous verification, from design time to runtime. Simulation is a highly-developed, time-honored design-time verification technique, whereas runtime verification is a much younger outgrowth from modern complex systems that both enable embedding analysis on-board and require mission-time verification, e.g., for flight certification. While the attributes of simulation are well-defined, the vocabulary of runtime verification is still being formed; both are active research areas needed to ensure safety and security. This invited paper explores the connections and differences between simulation and runtime verification and poses open research questions regarding how each might be used to advance past bottlenecks in the other. We unify their vocabulary, list their commonalities and contrasts, and examine how their artifacts may be connected to push the state of the art of what we can (safely) fly.