Communication endpoints, software update servers, and related methods are disclosed. A communication endpoint includes a data storage device including a boot loader partition, a boot loader settings partition, and a plurality of combo image partitions. A method includes receiving an update package including a new combo image and one or more repair modules configured to diagnose and repair at least one of a boot loader, boot loader settings, and a file system of the communication endpoint. The method also includes replacing a combo image stored on one of the plurality of combo image partitions with the new combo image, and executing at least one of the one or more repair modules. A software update server includes a data storage device including the update package, and communication elements configured to transmit the update package to the communication endpoint.