1. OpenSSL

1.1. Questions

1.1.1. Q1

A CA file has been bootstrapped using certificates from the SystemRoots
keychain. To add additional certificates (e.g. the certificates added in
the System keychain), place .pem files in
  /usr/local/etc/openssl/certs

and run
  /usr/local/opt/openssl/bin/c_rehash

This formula is keg-only, which means it was not symlinked into /usr/local.

Apple has deprecated use of OpenSSL in favor of its own TLS and crypto libraries

If you need to have this software first in your PATH run:
  echo 'export PATH="/usr/local/opt/openssl/bin:$PATH"' >> ~/.bash_profile

For compilers to find this software you may need to set:
    LDFLAGS:  -L/usr/local/opt/openssl/lib
    CPPFLAGS: -I/usr/local/opt/openssl/include
For pkg-config to find this software you may need to set:
    PKG_CONFIG_PATH: /usr/local/opt/openssl/lib/pkgconfig

Answer:

brew unlink openssl
brew install --force openssl
brew link openssl