Carbon Black. As a software developer, running unknown/untrusted binaries is kind of a big part of my job. We also had a MITM SSL-intercepting proxy which made my life miserable, especially when dealing with Docker containers. I actually ended up patching Docker to automatically inject the certificates and proxy environment variables.

On the plus side I learned a lot about certificate errors which has made me the go-to guy for any SSL issues in my current job.