This research focuses on the tax, financial reporting, and sustainability consequences that companies face as a part of settling agreement non-disclosure clauses for workplace sexual harassment claims and cases. Given recent events such as the sexual harassment cases of former Governor Andrew Cuomo and those in the entertainment industry like Harvey Weinstein, managers, and decision-makers must be able to justify decisions to include such clauses in a settlement agreement, and then require an external review of the facts, circumstances, practices, and institutional policies which helped lead to such claim(s). The recent change in legislation and regulation has impacted how companies can work to eliminate and combat sexual harassment cases in the workplace. Using contextual analysis, we first examine the tax considerations of non-disclosure clauses, post-adoption of I.R.C. §162(q), and subsequently review emerging financial reporting consequences of sexual harassment, and finally, we review sexual harassment in relation to the growing SRI movement and its focus on the two specific ESG factors related to governance and social issues. Our research proposes practical guidelines, considerations, and reforms for companies to manage tax, financial, public relations, and environmental, social and governance (ESG) elements associated with efforts to “weed out” sexual harassment behaviors within organizations.