A system and method for a cloud callback platform, comprising at least a profile manager, callback manager, interaction manager, media server, context analysis engine, and context aggregator mechanism, allowing users to call a business, agents in contact centers, or other users who are connected to cloud callback platform, and, failing to connect to the individual they called, or by request, allow for an automatic callback object to be created, whereby the two users may be automatically called and bridged together at a time when both users are available, and a context summary report is sent to one or more user. The system and method implement predictive logic to determine the most successful alternative communication channel to use to bridge the two parties.