A system for transactionally deploying content across multiple machines in a network environment automates and synchronizes secure and reliable distribution of digital assets to multiple network locations, allowing controlled provisioning and synchronization of code and content updates to live applications. A distributed architecture includes at least one receiver—a secure listener configured to process incoming distribution jobs—and at least one base server—a sender that may also act as a receiver. An administration interface allows administrative and reporting services and deployment management. Using the administrative interface, users are enabled to launch, simulate, schedule and monitor activities for any network location at any time. The system provides fan-out and multi-tiered deployment topologies expandable to hundreds of servers. Each deployment is fully transactional, permitting rollback of the system to it “last known good” state in the case of failure.