In this talk we will tell the story of an insane exploit we used to compromise the otherwise secure KASM Workspaces software. KASM Workspaces is enterprise software for streaming virtual workstations to end users built on top of Docker. This talk will span python binary RE, header smuggling, configuration injection, docker networking and questionable RFC interpretation. We hope to show you a little bit of what worked and a lot a bit of what didn't work on our quest to exploit this Heisenbug.