Yes, the large scale solution from Microsoft is System Center Configuration Manager, which I use extensively at work. SCCM has a lot of strengths, but it's not

Yes, the large scale solution from Microsoft is System Center Configuration Manager, which I use extensively at work. SCCM has a lot of strengths, but it's not really suited to small operations: it has a lot of complexity that smaller orgs simply wouldn't use. Doing something simple like pushing out the latest version of Firefox without customizations, aside from the time it takes to find and download the file, still takes a good number of steps afterwards. It's a sledgehammer when some people just need a mallet, and it also costs a good amount of money! Active Directory users can utilize Group Policy for software deployment, but that has its own share of caveats (I haven't used it in a while, but last I checked deployed apps have to be an MSI). The thing that appeals to me about Chocolately is that it does the work of going out and getting the package for you. If you're in an environment where you don't need to do any customization of packages, this seems like a way to save time and energy over using Group Policy. However, there doesn't seem to be any reporting capability nor is there a way to initiate deployments from a central server (I guess the idea is to designate a startup script in Group Policy or just have users type commands themselves). Even in a small environment, those two features really help with management. It'd be nice if there was a way to create a local distribution point in order to minimize bandwidth usage. But that would be a big project in itself...