I used to work for a company whose product was a specialized proxy server aimed at telco companies. The thesis was that telco companies (at the time, this was q

I used to work for a company whose product was a specialized proxy server aimed at telco companies. The thesis was that telco companies (at the time, this was quite some time ago) were heavy users of telnet and ssh to administer network devices, and needed some tooling to help manage them all. So our device would proxy telnet and ssh connections, and do things like looking at the hostname and the login prompt and automatically submit the correct credentials, and then further do things like blocking certain commands from being run, providing pre-configured scripts for certain tasks, yadda yadda yadda. Now that's all fine and good as such. I had no qualms about working on that stuff. But then somebody introduced the idea of capturing frequent screen-grabs (essentially video, albeit at a fairly low frame rate) of the user's desktop as they used the system. We worked out a way to do some weird windows network driver shenanigans to make sure the recording started when an outgoing connection was made to certain destinations, and then streamed the video to a server where it was stored. The nominal purpose for this was advertised as "training" with a side-dish of "compliance enforcement", and probably in some highly regulated industries people will (and do?) accept this sort of thing. But it never sat well with me, and I felt a bit queasy about working on that aspect of the product.