If you're using Homebrew /usr/local/bin should already be at the front of $PATH or at least come before /usr/bin. If you now run brew link --force openssl in your terminal window, open a new one and run which openssl in it. It should now show openssl under /usr/local/bin.

Answer from Olaf Heinemann on Stack Overflow
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Homebrew
formulae.brew.sh › formula › openssl@3
Homebrew Formulae: openssl@3
brew install openssl@3 · Also known as: openssl, openssl@3.6 · Cryptography and SSL/TLS Toolkit · https://openssl-library.org · License: Apache-2.0 · Development: Pull requests · Formula JSON API: /api/formula/openssl@3.json · Formula ...
Discussions

Homebrew Not installing openssl
OpenSSL is already included in MacOS. What is your reason for using Homebrew for this? 🙂 More on reddit.com
🌐 r/MacOS
8
2
May 12, 2022
Update OSX openssl requirement to openssl@3
Migrate formulae to openssl@3 Homebrew/homebrew-core#134251 · As a result, when we follow the security steps here (and install gpg using brew install gnupg), that will install openssl@3 as a brew dependency. When we then run rvm install 3.2.2 that will install openssl@1.1. More on github.com
🌐 github.com
25
August 5, 2023
Where does Brew install OpenSSL on OS X?
We added the following to the YML file, but Brew states OpenSSL is already installed. before_install: - | if [ "$TRAVIS_OS_NAME" = "osx" ]; then brew update brew install openssl fi The actual configure failure is: checking for SSL... configure: error: Cannot find the S... More on travis-ci.community
🌐 travis-ci.community
6
0
February 27, 2020
Building on macOS Ventura w/ Brew OpenSSL - SQLCipher - Zetetic Community Discussion
This caused me a bit of grief, so I thought I’d share the solution that worked for me (run from the sqlcipher code folder): brew install openssl BREW_OPENSSL_PATH=`ls -d '/usr/local/Cellar/openssl@3/'*` ./configure --enable-tempstore=yes CFLAGS="-DSQLITE_HAS_CODEC -L$BREW_OPENSSL_PATH/lib/ ... More on discuss.zetetic.net
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March 2, 2023
Top answer
1 of 3
3

IMO the best way to install openssl on MacOS is to use Homebrew. This will not only install openssl, but will also allow it to be upgraded in the future.

brew install openssl

If you want to make the Homebrew version the default (rather than the LibreSSL that comes with MacOS), you will also need put the Hombrew-installed openssl on your path ahead of the MacOS version. While it is possible to accomplish this by putting /opt/homebrew/bin on your PATH ahead of /usr/bin, I strongly discourage this, because it makes you vulnerable to unintentionally installing a malicious Homebrew package named something like ls that overrides your default ls with malicious code. Instead, my personal preference is to have a user-level directory where I maintain a small set of binaries that override the defaults.

# Create a user-level bin directory, if it doesn't already exist.
mkdir -p ~/bin

# Create a symlink to the Homebrew openssl, if such a symlink does not already exist
ln -fs /opt/homebrew/bin/openssl ~/bin/openssl

Then, put ~/bin on your PATH, ahead of /usr/bin. This part depends on which shell you are using. For bash, you can add this to your ~/.bash_profile.

# User-level binaries, manually added
PATH="${HOME}/bin:${PATH}"
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The first option is the simplest one: do nothing. macOS has shipped with OpenSSL preinstalled since 2000.

You can download a binary distribution of OpenSSL. The OpenSSL project does not itself publish binary releases, but they maintain a list of third-party resources that publish OpenSSL binaries.

You can install it using MacPorts.

You can install it using Homebrew.

You can compile it yourself. You already downloaded the source code, so all you need is to follow the instructions in the INSTALL.md file you are showing in your screenshot. I assume that, since you chose to use an inofficial development version, you may run into some bugs.

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Homebrew
formulae.brew.sh › formula › openssl@3.5
openssl@3.5 — Homebrew Formulae
brew install openssl@3.5 · Cryptography and SSL/TLS Toolkit · https://openssl-library.org · License: Apache-2.0 · Development: Pull requests · Formula JSON API: /api/formula/openssl@3.5.json · Formula code: openssl@3.5.rb on GitHub · ...
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Reddit
reddit.com › r/macos › homebrew not installing openssl
r/MacOS on Reddit: Homebrew Not installing openssl
May 12, 2022 -

I'm sure this is a stupid quetsion. But I just recived my new M1 Mac Pro and am working through setting up the basics. I am attempting to install openssl through homebrew, and it keeps not finding the package even though I'm pulling the command right from their website.

Here is the output of my terminal.

theworkinghamster ~ % brew install openssl

fatal: Could not resolve HEAD to a revision

Warning: No available formula with the name "openssl".

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Homebrew
formulae.brew.sh › formula › openssl@4
Homebrew Formulae: openssl@4
brew install openssl@4 · Cryptography and SSL/TLS Toolkit · https://openssl-library.org · License: Apache-2.0 · Development: Pull requests · Formula JSON API: /api/formula/openssl@4.json · Formula code: openssl@4.rb on GitHub · Bottle ...
🌐
GitHub
github.com › rvm › rvm › issues › 5380
Update OSX openssl requirement to openssl@3 · Issue #5380 · rvm/rvm
August 5, 2023 - rvm install 3.2.2 --with-openssl-dir=`brew --prefix openssl@3`
Author   rvm
Find elsewhere
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HPE Ezmeral
docs.ezmeral.hpe.com › datafabric-customer-managed › 80 › AdvancedInstallation › InstallingOpenSSL-for-mac-client.html
Installing OpenSSL for the Mac Client
OPENSSL_INSTALLED_LOCATION=`brew --prefix openssl@1.1` OPENSSL_LIBRARY_PATH=${OPENSSL_INSTALLED_LOCATION}/lib OPENSSL_PATH=${OPENSSL_INSTALLED_LOCATION}/bin export PATH=${OPENSSL_PATH}:${PATH} LD_LIBRARY_PATH=${OPENSSL_LIBRARY_PATH}:${LD_LIBRARY_PATH} Verify that the OpenSSL 1.1.1 binary is used.
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Travis CI Community
travis-ci.community › environments
Where does Brew install OpenSSL on OS X? - Environments - Travis CI Community
February 27, 2020 - We added the following to the YML file, but Brew states OpenSSL is already installed. before_install: - | if [ "$TRAVIS_OS_NAME" = "osx" ]; then brew update brew install openssl fi The actual configure failure is: checking for SSL... configure: error: Cannot find the S...
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Medium
maxim-ivanitskiy.medium.com › upgrade-openssl-for-macos-e7a9ed82a76b
Upgrade OpenSSL for MacOS. I needed to generate a self-signed… | by Maxim | Medium
February 5, 2020 - brew update brew upgrade brew install openssl mkdir -p /usr/local/lib ln -s /usr/local/opt/openssl/lib/libcrypto.1.0.0.dylib /usr/local/lib/ ln -s /usr/local/opt/openssl/lib/libssl.1.0.0.dylib /usr/local/lib/ brew link - force openssl
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Homebrew
formulae.brew.sh › formula › openssl@3.0
openssl@3.0 — Homebrew Formulae
brew install openssl@3.0 · Cryptography and SSL/TLS Toolkit · https://openssl-library.org · License: Apache-2.0 · Development: Pull requests · Formula JSON API: /api/formula/openssl@3.0.json · Formula code: openssl@3.0.rb on GitHub · ...
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GitHub
gist.github.com › darrenboyd › 58647ca3c31bd0ed4105
A quick guide to downgrading OpenSSL with Homebrew · GitHub
Download the file: https://github.com/tebelorg/Tump/releases/download/v1.0.0/openssl.rb · Run brew with the file downloaded: brew install openssl.rb
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FixMyCert
fixmycert.com › guides › openssl-installation
Install OpenSSL: Windows, Linux, macOS, Alpine
# Check the default openssl openssl version # Likely output: LibreSSL 3.3.6 # Check if Homebrew OpenSSL is installed brew list openssl 2>/dev/null && echo "Homebrew OpenSSL installed"
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Medium
yasar-yy.medium.com › installing-openssl-library-on-macos-catalina-6777a2e238a6
Installing OpenSSL library on macOS Catalina | by Yaşar Yücel Yeşilbağ | Medium
September 18, 2020 - We have to find library path of OpenSSL and add it to DYLD_LIBRARY_PATH environment variable. For this purpose, run “brew info openssl” command again. ... The path in the red rectangle at above screenshot is the path where OpenSSL is installed.
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Openssh
openssh.org
OpenSSH
OpenSSH 10.4 released July 6, 2026 · OpenSSH is the premier connectivity tool for remote login with the SSH protocol. It encrypts all traffic to eliminate eavesdropping, connection hijacking, and other attacks. In addition, OpenSSH provides a large suite of secure tunneling capabilities, several ...
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Franz Inc.
franz.com › support › openssl-mac.lhtml
Installing OpenSSL on macOS
The latest information on OpenSSL can be found in the installation guide.
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Qiita
qiita.com › mac
Homebrewとopensslのインストール #Mac - Qiita
May 3, 2018 - MacBook-Pro:/ mgr206$ echo 'export PATH=/usr/local/opt/openssl/bin:$PATH' >> ~/.bash_profile MacBook-Pro:/ mgr206$ source .bash_profile · brewでインストールしたopensslのPATHとバージョンになっています。
🌐
Zetetic
discuss.zetetic.net › sqlcipher
Building on macOS Ventura w/ Brew OpenSSL - SQLCipher - Zetetic Community Discussion
March 2, 2023 - This caused me a bit of grief, ... brew install openssl BREW_OPENSSL_PATH=`ls -d '/usr/local/Cellar/openssl@3/'*` ./configure --enable-tempstore=yes CFLAGS="-DSQLITE_HAS_CODEC -L$BREW_OPENSSL_PATH/lib/ ......
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Rust Programming Language
users.rust-lang.org › help
Help needed: OpenSSL, Mac OS, without Homebrew - help - The Rust Programming Language Forum
December 9, 2021 - If you have such experience, please write steps of resolving the OpenSSL issue on Mac OS without installing Homebrew. It would be the only reason I need Homebrew, so I'm trying to avoid it.