This paper presents a new stochastic methodology for evaluating and quantifying the downtime of a structure in terms of a family of fragilities that represent the probability of exceeding prescribed times to return to functionality. This methodology integrates several existing concepts, namely, Federal Emergency Management Agency P-58 and Resilience-based Earthquake Design Initiative (REDi), to build a family of system (building) level fragility curves corresponding to the time needed to achieve different recovery levels (reoccupancy, functional recovery, and full recovery). This approach enables one to propagate uncertainty throughout the procedure so that variations in the delay time and repair schedules are accounted for in the resulting fragilities. As an illustrative example of this approach, the methodology is applied to assess the downtime of a two-story mass timber building that was originally tested at the NHERI@UCSD outdoor shake table in 2017. One unique aspect of this analysis is that it incorporates a relatively new material, cross-laminated timber (CLT), in a resilient posttension rocking wall design application. Nonstructural components representing a typical office building were selected and incorporated into the procedure for the two-story CLT rocking wall building. Time-to-functionality fragility curves are then developed for the two-story building, and potential design and resilience-focused applications are discussed.