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.
Backups. Cloud services like Backblaze B2 are so cheap for the durability they offer, it just doesn’t make sense for me to roll my own offsite solution with a Raspberry Pi at my parents’ house or something. Restic encrypts everything before it leaves my machine.
Password manager- it’s too important and it’s the thing that has to work for me to recover when I break something else. I’m happy to support Bitwarden with a few bucks a year.
Email- again, it’s mission critical and I have a habit of tinkering with things and breaking them. And it’s just no fun. The less I need to think about email, the happier I am.