dyld: Library not loaded: /usr/local/opt/openssl/lib/libssl.1.0.0.dylib

by

Update: As of December 2020 and beyond, brew switch does not work, so use the other answer by @angabriel:

brew install rbenv/tap/[email protected]
ln -sfn /usr/local/Cellar/[email protected]/1.0.2t /usr/local/opt/openssl

Original Answer:
Switch to an older openssl package

brew switch openssl 1.0.2s

Or, depending on your exact system configuration, you may need to switch to a different version. Check the output of ls -al /usr/local/Cellar/openssl for the version number to switch to.

brew switch openssl 1.0.2q
# or
brew switch openssl 1.0.2r
# or 
brew switch openssl 1.0.2s
# or
brew switch openssl 1.0.2t
# etc...

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