Chocolatey is how I’ve moved software around Windows fleets for years, and it has
taught me plenty – some of it the hard way. This tag collects the posts on
packaging, building extensions, forcing reinstalls when a package won’t behave,
and the maintenance stories from running it at scale.
Practical package-management notes, aimed at anyone automating software delivery
on Windows.
Your Chocolatey package pipeline shouldn’t live in someone’s head. Learn how to automate Chocolatey packaging with psake — declared tasks, Pester tests, and CI/CD that runs identically locally and in GitHub Actions.
Learn how to force reinstall Chocolatey packages using PowerShell and packages.config. Complete walkthrough with XML generation script for handling partially removed packages.
Watch Gilbert’s Chocolatey Fest 2018 talk on maintenance mode at scale. Learn how Facebook’s IT team uses Chef to schedule service interruptions without impacting business operations.
