This paper addresses key normative questions related to the practice of law: In these days of digitized information, in which some lawyers’ only contact with their clients is through a narrow interface in which the lawyer is penalized for taking more than fifteen minutes to review a file, how do lawyers exercise independent professional judgment? When performing commoditized legal work, how do legal services providers ameliorate the systemic pressures for faster service and reductive outcome measures? Cautionary tales are emerging from evidence developed in connection with both criminal cases and civil litigation which reveal significant shortfalls in current structures in which services are delivered. Lawyers representing a number of creditors seeking judicial foreclosure in North American jurisdictions, for example, have submitted patently baseless documentation to courts, including robo-signed, forged and surrogate-signed affidavits. This paper assesses the role of regulation in ensuring that lawyers are able to resist client pressures in order to exercise their professional judgment. It also discusses ways to prepare law students to better handle these practice settings by incorporating a specific set of experiences into legal education, particularly in skills-developing courses and experiential learning opportunities.