Some embodiments relate to cutting element assemblies including a superabrasive cutting element that may be axially compressed to enhance the damage tolerance thereof, enclosed in an enclosure that exposes the superabrasive cutting element therethrough, enclosed in an enclosure that restricts rotation of the superabrasive cutting element, or combinations of the foregoing. Additionally, some embodiments relate to cutting element assemblies in which a superabrasive cutting element is mechanically fastened to a base, such as a substrate or directly to a bit body of a rotary drill bit. Some embodiments also relate to cutting element assemblies including one or more superabrasive cutting elements that are rotatable about a longitudinal axis of the cutting element assembly, that may be axially compressed to enhance the damage tolerance thereof, that may be enclosed in an enclosure that exposes the superabrasive cutting element therethrough, or combinations thereof.