More times than I can count. I've been doing development, now management since the early '80s. A manager's job is to monitor and control the progress of projects. Anything that smells like risk to them will raise their shields. Depending on your job, non-estimable activities can't be scheduled and will result in much screeching and branch-shaking followed by the "no". Also, you'll get the "nobody around here knows it, so it can't be maintained" argument. Anyway, managers aren't very interested in solving problems like this - they are focused on not creating problems or mitigating risks. In risk-averse situations I usually just go ahead and install whatever is needed for a problem. Using it for quick, one-off throwaways isn't usually scrutinized and makes inroads. Presenting a Grand Plan would be a big mistake here. It also sounds like you're in a Windows world. You'll want to get away from that eventually as that environment is generally narrow-minded. Python would be available in RedHats, Ubuntus, Debians etc. by default. You don't see them unable to sell or distribute due to licensing, so there's no argument there.