In 2020, DIDO© turned 20! The software package emerged in 2001 as a basic, user-friendly MATLAB teaching tool to illustrate the various nuances of Pontryagin’s Principle but quickly rose to prominence in 2007 after NASA announced it had executed a globally optimal maneuver using DIDO. Since then, the toolbox has grown in applications well beyond its aerospace roots: from solving problems in quantum control to ushering rapid, nonlinear sensitivity-analysis in designing high-performance automobiles. Most recently, it has been used to solve continuous-time traveling-salesman problems. Over the last two decades, DIDO’s algorithms have evolved from their simple use of generic nonlinear programming solvers to a more sophisticated employment of fast spectral Hamiltonian programming techniques. A description of the internal enhancements to DIDO that define its mathematics and algorithms are described in this paper. A challenge example problem from robotics is included to showcase how the latest version of DIDO is capable of escaping the trappings of a “local minimum” that ensnare many other trajectory optimization methods.