But if your tool is a non-licensed piece of software that then puts the company on the hook because you used it without people whose purview it is to know these things can cause problems.

I 100% understand the frustration of working in a place where lawyers "introduce drag". Lawyer's job isn't to make your job harder/easier, but to protect the company from whatever. Sometimes whatever turns out to be the "well intended" employee. Part of the friction in these situations are very zealous people wanting to do things while they are so scoped in on their task that they are unawares of the larger consequences to the company no matter how well intentioned they may be. As I've become older, I can corrolate that friction with youth. That coefficient of friction becomes smaller with age/experience. It has nothing to do with levels of caring/apathy, but from experiencing the negative affect of "move fast, break things" and being willing to tap the breaks a little bit while changing altitude to see a bigger picture.