I have a cherrypy app that I've made an exe with pyinstaller. now when I run the exe it loads itself twice into memory. Watching the taskmanager shows the first instance load into about 1k, then a second later a second instance of hte exe loads into about 3k ram. If I close the bigger one both processes die. If I close hte smaller one only that one dies.

Loading the exe with subprocess, if I try to proc.kill(), it only kills the small one leaving the other running in memory. Is this a sideeffect of using cherrypy and pyinstaller together?

PyInstaller spawns a subprocess during its boot process. This is explained in a section of its manual.