(base) localhost:~ ligaijiang$ brew install nmap Updating Homebrew... ==> Auto-updated Homebrew! Updated 1 tap (homebrew/services). No changes to formulae. ==> Installing dependencies for nmap: openssl ==> Installing nmap dependency: openssl ==> Downloading https://homebrew.bintray.com/bottles/openssl-1.0.2s.high_sierra.bottle.tar.gz ==> Downloading from https://akamai.bintray.com/b7/b72b8d9e582713d909936d7236542b366f07d800f8ec0eaa2d48 ######################################################################## 100.0% ==> Pouring openssl-1.0.2s.high_sierra.bottle.tar.gz ==> Caveats 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 openssl is keg-only, which means it was not symlinked into /usr/local, because Apple has deprecated use of OpenSSL in favor of its own TLS and crypto libraries. If you need to have openssl first in your PATH run: echo 'export PATH="/usr/local/opt/openssl/bin:$PATH"' >> ~/.bash_profile For compilers to find openssl you may need to set: export LDFLAGS="-L/usr/local/opt/openssl/lib" export CPPFLAGS="-I/usr/local/opt/openssl/include" ==> Summary 🍺 /usr/local/Cellar/openssl/1.0.2s: 1,795 files, 12.1MB ==> Installing nmap ==> Downloading https://homebrew.bintray.com/bottles/nmap-7.80.high_sierra.bottle.tar.gz ==> Downloading from https://akamai.bintray.com/14/14f1bf9bd3f84f5008f4a3005f3f6f245c4c23162f4b935c9afa ######################################################################## 100.0% ==> Pouring nmap-7.80.high_sierra.bottle.tar.gz 🍺 /usr/local/Cellar/nmap/7.80: 821 files, 27.0MB ==> `brew cleanup` has not been run in 30 days, running now... Removing: /Users/ligaijiang/Library/Caches/Homebrew/descriptions.json... (262.5KB) Removing: /Users/ligaijiang/Library/Logs/Homebrew/ant... (99B) Removing: /Users/ligaijiang/Library/Logs/Homebrew/geckodriver... (64B) Pruned 0 symbolic links and 2 directories from /usr/local ==> Caveats ==> openssl A CA file has been bootstrapped using certificates from the SystemRoots keychain. To add additional certificates (e.g. the certificates added in the System keychain), place .pem files in /usr/local/etc/openssl/certs and run /usr/local/opt/openssl/bin/c_rehash openssl is keg-only, which means it was not symlinked into /usr/local, because Apple has deprecated use of OpenSSL in favor of its own TLS and crypto libraries. If you need to have openssl first in your PATH run: echo 'export PATH="/usr/local/opt/openssl/bin:$PATH"' >> ~/.bash_profile For compilers to find openssl you may need to set: export LDFLAGS="-L/usr/local/opt/openssl/lib" export CPPFLAGS="-I/usr/local/opt/openssl/include" (base) localhost:~ ligaijiang$