You just want to connect to a remote Windows machine. Sometimes it "just works." Sometimes it doesn't and it's not clear why. We'll dissect some typical WinRM failures. I'll point out the questions to ask and some basic commands (for Windows and Linux) to run that will help you navigate your way to diagnosing your issue and hopefully leading to a successful connection. We'll look at the key points that influence WinRM connectivity and how they need to be configured to facilitate communication between nodes. We'll focus on some nuances specific to various Chef ecosystem tools that affect these settings and how you can configure these tools for the least amount of friction. What has changed and progressed in the last year with regards to the Ruby WinRM client used by knife-windows, Chef provisioning, Vagrant and Test Kitchen? How can you leverage these changes to provide a better remote experience? What works and does not work over WinRM and how can you work around the limitations?