Cloud-init is a Linux technology that allows easy setup and automation of virtual machines. The concept is very simple – the VM infrastructure provides some way of setting some custom data for each virtual machine (many providers call this “user data”), and when the operating system starts the cloud-init service reads that configuration, loads a bunch of modules to handle various parts and let them configure the system. As a user it is very convenient – you write a setup scenario using the variety of tools offered by cloud-init, you can store the scenario in a source control to allow to develop the scenario further, then just launch a bunch of machines with the specified scenario and watch them configure themselves.
The situation is much worse on the MS-Windows side of the fence: want to have an MS-Windows server configured and ready to go? Start a virtual machine, connect to is using RDP and Next, Next, Finish until your fingers are sore. Need to deploy a new version? either retrofit an existing image (again, manually) and risk deployment side effects, or do the whole process again from scratch.
Here’s a script to try to help a bit with the problem – at least on Amazon Web Services: a poor man’s cloud-init-like for MS-Windows server automation.