Semiconductor devices having an array of flexible connectors configured to mitigate thermomechanical stresses, and associated systems and methods, are disclosed herein. In one embodiment, a semiconductor assembly includes a substrate coupled to an array of flexible connectors. Each flexible connector can be transformed between a resting configuration and a loaded configuration. Each flexible connector can include a conductive wire electrically coupled to the substrate and a support material at least partially surrounding the conductive wire. The conductive wire can have a first shape when the flexible connector is in the resting configuration and a second, different shape when the flexible connector is in the loaded configuration.