As expectations rise for parenting plan evaluators to be well-trained, skilled, and knowledgeable in numerous subject areas, and scrutiny of evaluators’ work intensifies, the pool of qualified evaluators is shrinking nationwide. The future of parenting plan evaluation as a forensic subspecialty relies upon the availability of competent and committed professionals to do this challenging work, yet few are entering the field. Five experienced parenting plan evaluators from various regions of the United States, including the authors, met for a roundtable discussion to ponder the future of parenting plan evaluations. The panel discussed what drew them to the work, their experiences “in the trenches,” and what has kept them committed to doing evaluations despite daunting challenges. Their views of the rewards and risks of doing the work, barriers and disincentives to newcomers entering the field, recommendations to new evaluators, and outlook for the future are presented.