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Generating SSL Certificates on macOS

When generating SSL Certificates on macOS, you must ensure that you're using brew's openssl binary and not the one provided by the OS.

To do that, find out where your openssl is installed by running:

$ brew info openssl

You should see something like this:

[email protected]: stable 1.1.1i (bottled) [keg-only]
Cryptography and SSL/TLS Toolkit
https://openssl.org/
/usr/local/Cellar/[email protected]/1.1.1i (8,067 files, 18.5MB)
  Poured from bottle on 2020-12-11 at 11:31:46
From: https://github.com/Homebrew/homebrew-core/blob/HEAD/Formula/[email protected]
License: OpenSSL
==> Caveats
A CA file has been bootstrapped using certificates from the system
keychain. To add additional certificates, place .pem files in
  /usr/local/etc/[email protected]/certs

and run
  /usr/local/opt/[email protected]/bin/c_rehash

[email protected] is keg-only, which means it was not symlinked into /usr/local,
because macOS provides LibreSSL.

If you need to have [email protected] first in your PATH run:
  echo 'export PATH="/usr/local/opt/[email protected]/bin:$PATH"' >> /Users/flavio/.bash_profile

For compilers to find [email protected] you may need to set:
  export LDFLAGS="-L/usr/local/opt/[email protected]/lib"
  export CPPFLAGS="-I/usr/local/opt/[email protected]/include"

For pkg-config to find [email protected] you may need to set:
  export PKG_CONFIG_PATH="/usr/local/opt/[email protected]/lib/pkgconfig"

==> Analytics
install: 855,315 (30 days), 2,356,331 (90 days), 7,826,269 (365 days)
install-on-request: 139,236 (30 days), 373,801 (90 days), 1,120,685 (365 days)
build-error: 0 (30 days)

The important part is this:

echo 'export PATH="/usr/local/opt/[email protected]/bin:$PATH"' >> /Users/flavio/.bash_profile

Instead of running ./tests/server/ssl/generate.sh, you should instead run:

$ PATH="/usr/local/opt/[email protected]/bin ./tests/server/ssl/generate.sh

You should now be good to go.