In this presentation I discuss resilience and antifragility as behaviors resulting from the coupling of a system and its environment(s). Depending on the interactions between these two "ends" and on the quality of the individual behaviors that they may exercise, different strategies may be chosen: elasticity (change masking); entelechism (change tolerance); and antifragility (adapting to & learning from change). When the environment is very simple and only capable of so-called "random behavior", often the only effective strategy towards resilience is off-line dimensioning of redundancy as a result of a worst-case assessment of disturbances and/or threats. Much more complex and variegated is the case when both systems and environments are "intelligent" -- or at least able to exercise complex teleological and extrapolatory behaviors. In this case both system and ambient may choose among a variety of strategies in what could be regarded as a complex evolutionary game theory setting.