I ended up taking a slightly different route for anyone who is interested. Ansible has a hash filter | hash('sha256') , which I used to write the hashed value as a comment in the file. I then check for it's existence on subsequent runs and skip it if the values match. All things considered, it seems to work pretty well as a temporary solution. I may add some obfuscation to my technique but with a strong enough password and keeping strict permissions on the server.conf file, I'm okay with it for now. Regards, ... View more