5 min read This idea came to me when I was configuring Puppet Server to manage our Windows VMs. One thing that annoyed me for the longest time was having Notepad++ installed everywhere, and getting that popup that an update is available. Disabling the update check is not the solution. I realized that our server deployments are good. We build containers and automate installation of programs with package managers like Chocolatey on Windows and Yum on CentOS, and fully orchestrate servers and services. We can do something similar to keep our own personal computers’ software up-to-date using chocolatey, and without all the orchestration tech we usually needed. Basically just a scheduled task that runs a chocolatey script to keep our stuff up-to-date.