Recent published legal cases reflect an enhanced battle between medical experts over controlled substance prescribing and medical record documentation of the practitioner-patient relationship. Federal law still requires that controlled substances be prescribed by an individual practitioner 1) for a legitimate medical purpose and 2) who is acting in the usual course of professional practice and taking reasonable steps to prevent abuse and diversion. A recent DEA case stands out because of the agency’s enhanced focus on the sufficiency of medical record documentation in light of applicable licensing board requirements for opioid prescribing. The challenge of the COVID-19 public health emergency and the temporary “permission slip” offered by DEA for controlled substance prescribing through telemedicine encounters heightens the need for practitioner understanding of DEA and licensing board expectations in three key areas of chronic pain management: Patient History and Treatment Plans (MDL-05), Risk Evaluation and Updating Informed Consents and Treatment Agreements (MDL-06), and Periodic Review and Other Strategies During the COVID Era (MDL-07). Each of these courses builds upon the next and offers attendees a statement of “what” the DEA and licensing boards expect in terms of provider action and documentation, along with case-derived suggestions on “how” to evolve charting through the use of individualized care notes rather than boilerplate notes to render defensible provider documentation of clinical decision-making associated with controlled substance prescribing. This IS the Year of the Looking Glass and attendees will leave with a roadmap for self-evaluation to facilitate progress in the pursuit of quality pain care and improved medical record documentation.