CPS is primed to become a data-science driven field. As protein targets increase in size, synthetic challenges rapidly accumulate; however, an increasingly diverse chemical toolkit provides many solutions. As all protein targets and peptide segments are unique, every synthetic strategy requires deliberate planning and consideration of options, and our computational tools greatly assist with decision-making and visualization. The enhanced processing speed of our updated Aligator enables consideration of additional ligation junctions and provides overhead for more sophisticated segment evaluation in the future, such as aspartimide-forming potential, placement of quality-enhancing pseudoprolines and isoacyl dipeptides, 47 nuanced prediction of solubility and structure (as well as suggestions for temporary solubilizing tags ), and feedback from additional real-world CPS data to improve the accuracy of scores. With BracketMaker's framework to perform mathematical calculations with brackets, we now have a starting point for holistic consideration of an entire synthesis, and future efforts will be aimed at fully integrating the two programs (e.g., weighing bracket scores based on starting and intermediate segment properties). In future updates, the retrosynthetic analysis process of our bracket assembly tool could easily be adapted to other types of ligation chemistry, protecting groups, and side-chain modifications given a defined order of steps. Efforts to compile the varied methodology in existing CPS literature are already underway, and our standardized bracket format can assist with future database projects.