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.
One of the big problems with JIRA is it’s extremely configurable, so your experience depends entirely on how your admins have set it up. If your company is the type to micromanage, JIRA gives them a lot of tools to do that, which I think is why it gets so much hate from devs. I find it tolerable in my current job but it’s definitely designed for managers and not for developers.