A programming initiator device identifies a set of user devices for which an update to software/firmware/content has not yet been installed; wirelessly provides to one or a subset of the user devices the update and also instructions for how to distribute the update among remaining user devices of the set; and identifies from feedback wirelessly received from at least one of the user devices in the set all of the user devices of the set which have successfully installed the update. A first user device wirelessly receives an update to software/firmware/content and distribution information for distributing the update to at least a second user device; installs the update itself; and shares the update with the at least second user device according to the received distribution information.