Figured it out! Apparently this issue was with net-ssh gem. I had version 2.8.0 installed recently with some updates to my development environment and was the cause.
I’m not sure why it was failing, but gem uninstall net-ssh -v 2.8.0< fixed it for me.
If anyone actually knows why this was an issue or how I can correct this issue with the newer version of net-ssh I’d be interested to hear it.