This made me laugh :-) Grandparent is probably happy to just fly under the radar. The suggested conversation would probably play out thusly:
> IT! You idiots! Your dumb policies are forcing me to use this insecure software! Look how many vulnerabilities it has had over the years!
>> Hold up. Rewind. What's this software that you've installed?
> It's called PuTTY. And if you just change this policy I could...
>> And how insecure is it?
> Just check out all these vulnerabilities! It's probably not worse than the average, but it's unnecessary extra attack surface area that...
>> I'm going to need you to uninstall that. Now. And I'll need confirmation via email that you have done so by EOB, with your boss and the CISO on CC.
> But if you just change this boneheaded policy...
>> Now, please. We have a security incident on our hands. We can discuss policy another time. Is there anything else installed on your laptop that I should be aware of?