Computer-based methods and systems for performing automated distribution of a software package to one or more target machines in one or more regions of a distributed network of target machines, comprises the following steps. First, a base software package is prepared for each of the one or more regions based on at least one of: (i) policy data indicating which of the one or more regions are candidates for receiving the software package, (ii) dependency information indicating requisites for a service provided by the software package, and (iii) configuration information for each of the candidate regions. The base software package is then distributed to each of the candidate regions of the distributed network. The base software package received at each of the candidate regions is then customized based on at least one of: (i) regional distribution policies, (ii) dependency information specific to one or more roles performed by the target machines in that region, and (iii) individual target machine configuration information. Lastly, the software package customized in each of the candidate regions is distributed to at least one of the target machines in the candidate regions of the distributed network.