The mechanical behavior of sustainable (“green”), bio-based cellulose hollow fiber membranes (hereafter, hollow fiber) produced using green solvent, which is potential for desalination and solvent-resistant nanofiltration, can be evaluated either in dry or water-conditioned (wet) states. However, the effect of conditioning time on the mechanical behavior of hollow fibers has not been conclusive. In this work, an extensive evaluation involving an experimental campaign and rigorous application of statistical models for cellulose hollow fibers produced using green solvent (1-ethyl-3-methylimidazolium diethyl phosphate or [EMIM][DEP]) via a dry-jet spinning technique is reported. First, we evaluated the microstructures and separation performance (water permeation, solute rejection) of hollow fibers made of different cellulose concentrations (10–15 wt%) in both pristine and conditioned states. Then, the strength, stiffness, and ductility of hollow fiber samples of different gauge lengths (25 and 50 mm) were measured by a standard tensile test device. Here, the effect of conditioning time on mechanical properties was evaluated after the hollow fiber samples were water-immersed at different times (from 30 s to 2 months). The strength distribution of conditioned hollow fibers was modeled and analyzed using two-parameter and three-parameter Weibull models. Our results showed that the cellulose content of 15 wt% in the hollow fibers produced a denser microstructure, providing the lowest molecular weight cut-off (MWCO). The cellulose content and gauge length slightly modified the mechanical properties of hollow fibers when they were evaluated in pristine, dry conditions. The mechanical properties of hollow fibers were drastically reduced after 10 min of water immersion, beyond which their properties were stabilized. Weibull modeling of mechanical reliability showed that two- or three-parameter Weibull could estimate the failure probability of hollow fibers quite well. Nonetheless, the three-parameter Weibull is better than the two-parameter one in terms of accuracy in determining the threshold strength located at the “lower-end tail.” Our analysis provides a rigorous demonstration of Weibull modeling in evaluating the time-dependent mechanical behavior of ductile, cellulose-based hollow fiber membranes, which is essential to support the design and development of future hollow fiber membranes in desalination industries.