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

Updating OpenSSL to 1.1.1 on MacOS - Stack Overflow
The new LTS 1.1.1 version of OpenSSL is out. ... brew update brew install openssl@1.1 echo 'export PATH="$(brew --prefix)/opt/openssl@1.1/bin:$PATH"' >> ~/.bash_profile # Verify openssl version # OpenSSL 1.1.1c 28 May 2019 More on stackoverflow.com
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security - How to upgrade OpenSSL in OS X? - Ask Different
Today the heartbleed OpenSSL exploit ... and steal passwords). This affects OpenSSL versions including 1.0.1f which is the version on my · up-to-date Mavericks computer Mac (because I used port/brew to install other software which updated my openssl without me realizing ... More on apple.stackexchange.com
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April 8, 2014
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
How to properly upgrading openssl with Homebrew? - Server Fault
I just resolved a dependency issue in some software installed via Homebrew so the outdated openssl 1.1 can finally be removed. I did that with brew uninstall openssl@1.1 and it warned brew uninstall More on security.stackexchange.com
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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
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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 - $ /usr/bin/openssl version -a LibreSSL 2.2.7 built on: date not available platform: information not available options: bn(64,64) rc4(ptr,int) des(idx,cisc,16,int) blowfish(idx) compiler: information not available OPENSSLDIR: "/private/etc/ssl" The first thing we need to do is install brew if it is not installed. $ /usr/bin/ruby -e "$(curl -fsSL https://raw.githubusercontent.com/Homebrew/install/master/install)" ... 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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Server Fault
serverfault.com › questions › 1176925 › how-to-properly-upgrading-openssl-with-homebrew
How to properly upgrading openssl with Homebrew? - Server Fault
March 23, 2025 - I just resolved a dependency issue in some software installed via Homebrew so the outdated openssl 1.1 can finally be removed. I did that with brew uninstall openssl@1.1 and it warned brew uninstall
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Medium
katopz.medium.com › how-to-upgrade-openssl-8d005554401
How to upgrade OpenSSL (macOS). Problem : OpenSSL Security Advisory… | by katopz | Medium
January 20, 2017 - $ sudo rm /usr/bin/openssl · Install Homebrew if you didn’t have · $ /usr/bin/ruby -e "$(curl -fsSL https://raw.githubusercontent.com/Homebrew/install/master/install)" Or update if you already have · $ brew update && brew upgrade · Install ...
Find elsewhere
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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
brew install rbenv/tap/openssl@1.0 rvm reinstall 1.9.3-p551 --with-openssl-dir='/usr/local/opt/openssl@1.0' gem update --system
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Ruby on Mac
rubyonmac.dev › openssl-1-1-deprecated-how-this-affects-your-ruby-projects
OpenSSL 1.1 is deprecated: how this affects your Ruby projects | Ruby on Mac
3 weeks ago - UPDATE: OpenSSL 1.1 has now been disabled by Homebrew as of October 24, 2024. If you don’t already have OpenSSL 1.1 installed, and you’re having trouble installing Ruby, these posts might be more helpful: OpenSSL 1.1 has been disabled because ...
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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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GitHub
gist.github.com › a9f353a7a4a966cabc820138e12a7e33
Upgrade openssl on Mac · GitHub
Upgrade openssl on Mac. GitHub Gist: instantly share code, notes, and snippets.
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GitHub
github.com › orgs › Homebrew › discussions › 4344
now that OpenSSL 3.1 is out, how do I install OpenSSL 3.0? · Homebrew · Discussion #4344
curl -L https://raw.githubusercontent.com/Homebrew/homebrew-core/e68186ba5a05a6ea9a30d6c7744de9a46bd3aadd/Formula/o/openssl@3.rb > openssl@3.rb · hey @vesper8 how did you find out this link to install 3.1.4 version? I need to install exactly the 3.2.0 version and I am not sure where to look at. to contextualize: I am trying to create postgis extension on a postgres database; I've run brew install postgis to install dependency but brew also updated my openssl version to 3.3 which was (unfortunate for me) launched this month and now I get the following error when trying to CREATE EXTENSION postgis:
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GitHub
github.com › actions › virtual-environments › issues › 664
Use `brew upgrade openssl@1.1` to update OpenSSL breaks Python 3.8 install on macOS · Issue #664 · actions/runner-images
April 3, 2020 - Describe the bug The following sequence of steps leads to a broken Python: uses: actions/setup-python@v1 with: python-version: "3.8" - run: brew update - run: brew upgrade openssl@1.1 - r...
Author   actions
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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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Fossil
fossil-scm.org › forum › forumpost › 9496e81a51
Fossil User Forum: Missing Homebrew OpenSSL path check on M1 Macs
The core problem here is that Apple hasn't shipped an up-to-date OpenSSL in years and years, probably part of this whole anti-GPL thing they've got going on, so we've got to go digging for third-party installs. I've got an M1 coming, but it's somewhere between here and China at the moment. Maybe someone will beat me to a well-considered fix before it arrives. Running brew install openssl@1.1 ends up creating both
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GitHub
gist.github.com › zulhfreelancer › 4a609f65dfc396e395e5d5713fb3dd0f
How to switch OpenSSL version on Mac using Homebrew? · GitHub
$ ls -al /usr/local/Cellar/openssl* /usr/local/Cellar/openssl: total 0 drwxr-xr-x 13 zulhilmi staff 442 Apr 21 04:31 1.0.2t /usr/local/Cellar/openssl@1.1: total 0 drwxr-xr-x 13 zulhilmi staff 442 Apr 21 04:01 1.1.1f drwxr-xr-x 13 zulhilmi staff 442 Apr 24 15:41 1.1.1g ... This worked for me. I unlinked the current version using $brew unlink openssl@1.0 Then i linked the version i need to use using $brew link openssl@1.1 Finally i checked the openssl version and i got OpenSSL 1.1.1w 11 Sep 2023