Auditors review documented financial figures to test for their accuracy and materiality. Lawyers analyze evidential facts and records to build sound legal arguments. These parties work toward a mutual purpose: to present their clients as legitimate and compliant businesses. But what happens when the concrete facts upon which lawyers and auditors base their work are obscured by their inability to see into the future? In other words, how can these professions conjunctively handle potential future obligations brought about by contingent liabilities? This study will attempt to resolve the tensions that emerge between lawyers and auditors when tasked with estimating the likelihood and financial value of contingent liabilities. It considers the strict regulations set forth by the ABA and FASB and how each side might circumvent the guidelines to allow for better collaboration. Addressing a focal point of contention between the legal and financial professions for decades, this study will also look at past attempts at mediating the conflict as well as current proposals to alter the contingent liability disclosure process. Most importantly, it distinguishes itself from prior research by implementing firsthand arguments from professionals in each field to improve the cooperative landscape. Collectively weighing previously attempted solutions, current regulatory barriers, and professional guidance, this study proposes a three-step solution toward initiating reform between lawyers and auditors to enhance the visibility, precision, and ease of disclosing contingent liabilities.