An apparatus to facilitate matchmaking-based enhanced debugging for microservices architectures is disclosed. The apparatus includes one or more processors to: detect, by an anomaly detector in a sidecar of a microservice hosted by a container, an anomaly in telemetry data generated by the microservice, the microservice hosted in a container executed by the processor and part of a service of an application; enable, by an enhanced debug and trace component of the sidecar, a debug mode in the microservice, the debug mode based on a type of the anomaly; collect, by the enhanced debug and trace component, a target set of data points generated by the microservice; and process, by the enhanced debug and trace component, the target set of data points with a matchmaking process to generate a timestamp and a tag for a context for each data point of the target set of data points.