Computer-implemented methods, media, and systems for context-sensitive defragmentation and aggregation of containerized workloads running on edge devices are disclosed. One example method includes monitoring telemetry data from multiple software defined wide area network (SD-WAN) edge devices that run multiple workloads, where the telemetry data includes at least one of resource utilization at the multiple SD-WAN edge devices, inter-workload trigger dependency, or inter-workload data dependency among the multiple workloads. It is determined, based on the telemetry data, that at least two of the multiple workloads running on at least two SD-WAN edge devices have the inter-workload trigger dependency or the inter-workload data dependency. In response to the determination that the at least two of the multiple workloads have the inter-workload trigger dependency or the inter-workload data dependency, a first process of migrating the at least two of the multiple workloads to a first SD-WAN edge device of is initiated.