I'm not sure if this entirely qualifies and I might have ranted about it a few years ago but fuck it.

My last internship. Company was awesome and my mentor/technical manager got along very well with me to the point that he often asked me to help out with Linux based stuff (he preferred Linux but was a C# guy and wasn't as familiar with it as me (Linux)).

We had to build an internal site thingy (don't remember what it was) and we delivered (me and some interns) and then the publishing moment came so I went to out project manager (a not-as-technical one) and asked if he could install a LetsEncrypt certificate on the site (he knew how and was one of the only ones who had direct access to the server).

He just stared at us and asked why the fuck we needed that since it was an internal thing anyways.
I kindly told that since it's free and can secure the connection, I preferred that and since its more secure, why the fuck not?
He wasn't convinced so it was off.

Next day I came in early and asked my mentor if he could do the SSL since he usually had access to that stuff. He stared at me with "what?" eyes and I explained what the PM said.

Then he immediately ssh'd in and got the damn cert with "we're going to go secure by default, of course!"

A minute later it was all set.