Methods and apparatus for smoothly and efficiently upgrading set top boxes, e.g., personal video recorders, which have customer selected content stored thereon are described. The described methods allow content stored on a set top box to be uploaded to a network storage device, e.g., automatically at a predetermined time prior to a scheduled upgrade, or in some cases, via manual control of the set top box to be upgraded. After stored content is uploaded to the network storage device, the set top box is replaced with a new set top box. The new set top box can be preloaded with the previously uploaded content or a content download can be triggered, e.g., by activating a hidden application and by supplying information identifying the set top box being replaced as part of the upgrade process.