A lighting system includes lighting devices and an update manager. The lighting devices include various hardware versions and/or functionalities. The lighting devices are queried to determine existing hardware versions and/or functionalities. The query is sent via a wireless mesh network of the lighting system. An Over-The-Air (OTA) update includes multiple different lighting device programming images, where each image corresponds to one of the existing hardware versions and/or functionalities. The OTA update is delivered via point-to-point connections between the update manager and some number of lighting devices and/or between the lighting devices. Upon receipt, individual lighting devices determine whether a lighting device programming image is needed and/or which of the lighting device programming images is appropriate.