The year 2021 was the most deadly year for overdose deaths in the USA and Canada. The stress and social isolation stemming from the COVID-19 pandemic coupled with a flood of fentanyl into local drug markets created conditions in which people who use drugs were more susceptible to accidental overdose. Within territorial, state, and local policy communities, there have been longstanding efforts to reduce morbidity and mortality within this population; however, the current overdose crisis clearly indicates an urgent need for additional, easily accessible, and innovative services. Street-based drug testing programs allow individuals to learn the composition of their substances prior to use, averting unintended overdoses while also creating low threshold opportunities for individuals to connect to other harm reduction services, including substance use treatment programs. We sought to capture perspectives from service providers to document best practices around fielding community-based drug testing programs, including optimizing their position within a constellation of other harm reduction services to best serve local communities. We conducted 11 in-depth interviews from June to November 2022 via Zoom with harm reduction service providers to explore barriers and facilitators around the implementation of drug checking programs, the potential for integration with other health promotion services, and best practices for sustaining these programs, taking the local community and policy landscape into account. Interviews lasted 45–60 min and were recorded and transcribed. Thematic analysis was used to reduce the data, and transcripts were discussed by a team of trained analysts. Several key themes emerged from our interviews: (1) the instability of drug markets amid an inconsistent and dangerous drug supply; (2) implementing drug checking services in dynamic environments in response to the rapidly changing needs of local communities; (3) training and ongoing capacity building needed to create sustainable programs; and (4) the potential for integrating drug checking programs into other services. There are opportunities for this service to make a difference in overdose deaths as the contours of the drug market itself have changed over time, but a number of challenges remain to implement them effectively and sustain the service over time. Drug checking itself represents a paradox within the larger policy context, putting the sustainability of these programs at risk and challenging the potential to scale these programs as the overdose epidemic worsens.