The illicit drug overdose crisis in North America continues to devastate communities with fentanyl detected in the majority of illicit drug overdose deaths. The COVID-19 pandemic has heightened concerns of even greater unpredictability in the drug supplies and unprecedented rates of overdoses. Portable drug-checking technologies are increasingly being integrated within overdose prevention strategies. These emerging responses are raising new questions about which technologies to pursue and what service models can respond to the current risks and contexts. In what has been referred to as the epicenter of the overdose crisis in Canada, a multi-technology platform for drug checking is being piloted in community settings using a suite of chemical analytical methods to provide real-time harm reduction. These include infrared absorption, Raman scattering, gas chromatography with mass spectrometry, and antibody-based test strips. In this Perspective, we illustrate some advantages and challenges of using multiple techniques for the analysis of the same sample, and provide an example of a data analysis and visualization platform that can unify the presentation of the results and enable deeper analysis of the results. We also highlight the implementation of a various service models that co-exist in a research setting, with particular emphasis on the way that drug checking technicians and harm reduction workers interact with service users. Finally, we provide a description of the challenges associated with data interpretation and the communication of results to a diverse audience.