Issues with Cloudflare CA certificate installation instructions for RubyGems

[lukevalenta]

trafficstars

Which Cloudflare product does this pertain to?

Zero Trust

Existing documentation URL(s)

• https://developers.cloudflare.com/cloudflare-one/connections/connect-devices/warp/user-side-certificates/install-cloudflare-cert/#rubygems

What changes are you suggesting?

There are two issues with the instructions for installing the Cloudflare root CA in rubygems.

1. See https://gist.github.com/joseluisq/e3b2f43e7e2453b2a84c for details, but the command gem which rubygems returns a file rubygems.rb, and the suffix needs to be trimmed. In bash or zsh, the following change should work:

export RUBY_DIR=$(gem which rubygems)

to

export RUBY_DIR=${$(gem which rubygems)%.rb}

The corresponding instructions for Windows should also be fixed.

2. On macOS Sonoma (14.3.1), my rubygems path is as follows:

/System/Library/Frameworks/Ruby.framework/Versions/2.6/usr/lib/ruby/2.6.0/rubygems/ssl_certs/rubygems.org/

However, I get Operation not permitted when trying to copy a file into that directly (even when run with sudo and enabling Full Disk Access to my terminal application). Based on https://cleanmymac.com/blog/operation-not-permitted-terminal, this seems to require disabling System Integrity Protection (SIP), but I haven't tried it. I'm not sure if we should recommend these steps, but I just wanted to report this issue.

Additional information

No response