Oh, how I have learned the hard way on this. Our IT now blocks outbound SSH entirely. You know, the secure way to access VM's in, say, our cloud? Sigh. I'm sur

Oh, how I have learned the hard way on this. Our IT now blocks outbound SSH entirely. You know, the secure way to access VM's in, say, our cloud? Sigh. I'm sure there's a "jump" server somewhere that I'd have to log into, `sudo` to another account, THEN SSH to my target box. Whatever. I just avoid the VPN. I used to use `cntlm` to tunnel requests through our firewall for things like Ruby's bundler, as it required NTLM authentication. Now they've also gone the additional mile, and installed a certificate (Cisco Umbrella) in all of our computers, and require its signature to pass the firewall. Unfortunately, it took me a long time to sort this out: why `cntlm` no longer worked, and why none of the usual suggestions on SO fixed it. I finally figured out that RubyInstaller for Windows included a nice facility to deal with this. You just place additional certs in a directory, run a Ruby script, and it will bundle the whole stack into a single .pem, which it will reference for all network-related commands. Thankfully, bundler's error messages were telling me the specific certs I needed, and I could download them from Cisco's web site. Just about a month ago, my company started requiring that cert for ALL traffic, not just HTTP(S). Like for, say, Postgres connections on port 5432. I finally realized that I could reference that same SSL bundle in my Postgres client connections, and get through. I've spent about 8 years here now, and it's been a cat-and-mouse game the whole time. I'm always wondering what's coming next.