We consider group sequential design supporting multiple objectives and possibly including complexities such as non-proportional hazards due to a delayed treatment effect. Given that off-the-shelf software has limited capabilities, we have supported a multiple open source R packages to support complex designs. The gsDesign2 package supports design and analysis under non-proportional hazards assumptions. For testing multiple hypotheses using graphical multiplicity method, the gMCPLite package supports graphs and provides examples for how to analyze trials with multiple objectives. For trials testing hypotheses for multiple overlapping populations or testing of multiple experimental treatment groups versus a common control, the wpgsd package takes advantage of known correlations to efficiently test hypotheses. Finally, the simtrial package is a fast simulation tool for time-to-event endpoints. In addition to describing key package capabilities, we describe our processes to justify use in a regulatory compliant environment.