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}"
Answer from Cameron Hudson on Stack Exchange
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MacPorts
ports.macports.org › port › openssl
Install openssl on macOS with MacPorts
To install openssl, run the following command in macOS terminal (Applications->Utilities->Terminal)
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GitHub
gist.github.com › byronmansfield › 97d74d8b0d1ea28b48536020dbd6d53e
Install OpenSSL from source Mac OS X · GitHub
Would you happen to have a suggestion on how to get past this issue? ... Here is what worked for me: sudo make install MANDIR=/usr/local/openssl/share/man MANSUFFIX=ssl That completed fine.
Discussions

macos - How to install latest version of openssl Mac OS X El Capitan - Stack Overflow
I have used brew install openssl to download and install openssl v1.0.2f, however, it comes back saying: A CA file has been bootstrapped using certificates from the system keychain. To add additio... More on stackoverflow.com
🌐 stackoverflow.com
OPENSSL@3 and Monterey - Fickle Pa… | Apple Developer Forums
Does anyone maintain local virtual servers with local domain names and SSL security? If so please read on. I use OPENSSL@3 installed by Homebrew in a MacOS Monterey environment with Xcode working in the background to create a series of keys and certificates (see below) so that I can open my ... More on developer.apple.com
🌐 developer.apple.com
Openssl install failure on MacOS Monterey M1 (arm64) for R 4.2.0 ("Vigorous Calisthenics") - Stack Overflow
I recently upgraded my R version to the latest release (4.2.0, 2022-04-22). I am receiving this error message when installing openssl package. I have tried installing from both CRAN and GitHub. Thi... More on stackoverflow.com
🌐 stackoverflow.com
macOS Monterey: installation failures with RVM, ASDF, rbenv caused by openssl/homebrew settings
Reload to refresh your session. You switched accounts on another tab or window. Reload to refresh your session. ... There was an error while loading. Please reload this page. ... macOS Monterey: installation failures with RVM, ASDF, rbenv caused by openssl/homebrew settings#17885 More on github.com
🌐 github.com
3
March 15, 2022
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}"
2 of 3
2

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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Mac App Store
macappstore.org › home › install openssl on mac osx
Install openssl on Mac OSX - Mac App Store
June 12, 2022 - Copy and paste the following command in Terminal app: /bin/bash -c "$(curl -fsSL https://raw.githubusercontent.com/Homebrew/install/HEAD/install.sh)" and press enter/return key. Wait for the command to finish. If you are prompted to enter a password, please type your Mac user's login password ...
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LEMP
lemp.io › how-to-install-openssl-on-mac-os-x-sierra
How To Install OpenSSL On Mac OS X Sierra
March 16, 2022 - Configuring a fast web server in the current hosting landscape requires attention to several performance and security details beyond basic installation. Enable HTTP/2 in your Nginx configuration to allow multiplexed connections that load pages faster. Configure Gzip or Brotli compression to reduce the size of text-based responses including HTML, CSS, JavaScript, and JSON.
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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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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 ...
Find elsewhere
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print "Me"
riffraff.info › home › ruby, rvm, macports and openssl on macos (monterey)
Ruby, RVM, MacPorts and OpenSSL on macOS (Monterey) - print "Me"
October 5, 2022 - In theory --with-openssl-dir should be enough, but AFAIU MacPorts puts stuff in separate directories which does not play well with ruby-build. Which is fair, as ruby-build does not explicitly support MacPorts, but rather homebrew. Anyway, once this is solved you may still encounter issues when installing gems that depend on OpenSSL, as those will also need to be told where OpenSSL is.
🌐
Apple Developer
developer.apple.com › forums › thread › 709931
OPENSSL@3 and Monterey - Fickle Pa… | Apple Developer Forums
Does anyone maintain local virtual servers with local domain names and SSL security? If so please read on. I use OPENSSL@3 installed by Homebrew in a MacOS Monterey environment with Xcode working in the background to create a series of keys and certificates (see below) so that I can open my local sites with the https:// prefix.
🌐
Stack Overflow
stackoverflow.com › questions › 72264628 › openssl-install-failure-on-macos-monterey-m1-arm64-for-r-4-2-0-vigorous-cali
Openssl install failure on MacOS Monterey M1 (arm64) for R 4.2.0 ("Vigorous Calisthenics") - Stack Overflow
ink with file built for macOS-x86_64 installing to /Library/Frameworks/R.framework/Versions/4.2-arm64/Resources/library/00LOCK-openssl/00new/openssl/libs ** R ** inst ** byte-compile and prepare package for lazy loading ** help *** installing help indices ** building package indices ** installing vignettes ** testing if installed package can be loaded from temporary location Error: package or namespace load failed for ‘openssl’ in dyn.load(file, DLLpath = DLLpath, ...): unable to load shared object '/Library/Frameworks/R.framework/Versions/4.2-arm64/Resources/library/00LOCK-openssl/00new/o
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Roger's Blog
blog.luojia.work › posts › Learning › Install openssl Manually on MacOS.html
Install openssl Manually on MacOS | Roger's Blog
January 13, 2025 - brew uninstall openssl wget https://www.openssl.org/source/openssl-3.4.0.tar.gz tar -xvf openssl-3.4.0.tar.gz cd openssl-3.4.0 ./Configure darwin64-arm64-cc make sudo make install MANDIR=/opt/homebrew/Cellar/openssl@3/3.4.0/share/man MANSUFFIX=ssl sudo mkdir /opt/homebrew/Cellar/openssl@3/3.4.0/bin sudo mv /usr/local/bin/openssl /opt/homebrew/Cellar/openssl@3/3.4.0/bin/openssl ls -s /opt/homebrew/Cellar/openssl@3/3.4.0/bin/openssl /usr/local/bin/openssl sudo mv /usr/local/share/doc /opt/homebrew/Cellar/openssl@3/3.4.0/share/doc sudo mv /usr/local/include /opt/homebrew/Cellar/openssl@3/3.4.0/include sudo mv /usr/local/lib /opt/homebrew/Cellar/openssl@3/3.4.0/lib sudo mv /usr/local/ssl /opt/homebrew/Cellar/openssl@3/3.4.0/ssl brew linke openssl@3
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GitHub
gist.github.com › andyjack › 7dd4d7b65d262b2a6e56
Installing Net::SSLeay with openssl from homebrew (macOS)
If you installed openssl with brew without powers to install system-wide, you have to find your brew Cellar to link to instead, e.g. ... Then you can modify the CONFIG_ARGS shown above. Obviously the Perl library relies on you not upgrading your openssl out from under it! ... I had to use this in Monterey following what @nerdstrike suggested: /opt/homebrew/Cellar/openssl@1.1/1.1.1l_1/
🌐
Medium
katopz.medium.com › how-to-upgrade-openssl-8d005554401
How to upgrade OpenSSL (macOS). Problem : OpenSSL Security Advisory… | by katopz | Medium
January 20, 2017 - $ /usr/bin/ruby -e "$(curl -fsSL https://raw.githubusercontent.com/Homebrew/install/master/install)" ... Warning: Refusing to link: openssl Linking keg-only openssl means you may end up linking against the insecure, deprecated system OpenSSL while using the headers from Homebrew’s openssl.
🌐
GitHub
github.com › openssl › openssl › issues › 17885
macOS Monterey: installation failures with RVM, ASDF, rbenv caused by openssl/homebrew settings · Issue #17885 · openssl/openssl
March 15, 2022 - But none of the proposed solutions worked anymore for masOS Monterey 12.3, Apple M1 chip. The current XCode version: Version 13.3 (13E113). Nevertheless, I installed successfully Ruby 3.1.0 version with rvm: ➜ ~ rvm list =* ruby-3.1.0 [ arm64 ] # => - current # =* - current && default # * - default ... ➜ ~ openssl version -a OpenSSL 3.0.1 14 Dec 2021 (Library: OpenSSL 3.0.1 14 Dec 2021) built on: Tue Dec 14 16:16:25 2021 UTC platform: darwin64-arm64-cc options: bn(64,64) compiler: clang -fPIC -arch arm64 -O3 -Wall -DL_ENDIAN -DOPENSSL_PIC -D_REENTRANT -DOPENSSL_BUILDING_OPENSSL -DNDEBUG OPENSSLDIR: "/opt/homebrew/etc/openssl@3" ENGINESDIR: "/opt/homebrew/Cellar/openssl@3/3.0.1/lib/engines-3" MODULESDIR: "/opt/homebrew/Cellar/openssl@3/3.0.1/lib/ossl-modules" Seeding source: os-specific CPUINFO: OPENSSL_armcap=0x7f
Author   openssl
🌐
HPE Ezmeral
docs.ezmeral.hpe.com › datafabric-customer-managed › 80 › AdvancedInstallation › InstallingOpenSSL-for-mac-client.html
Installing OpenSSL for the Mac Client
OPENSSL_INSTALLED_LOCATION=`brew --prefix openssl@1.1` OPENSSL_LIBRARY_PATH=${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. Issuing the following command should return Open SSL 1.1.1x: openssl version OpenSSL 1.1.1l 24 Aug 2021 If the openssl version command returns LibreSSL, your configuration settings are incorrect: ... /opt/mapr/server/verify_ossl Unable to load OpenSSL from specified locations.
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Macupdate
openssl.macupdate.com › security › encryption & decryption
Download OpenSSL for Mac | MacUpdate
To install the OpenSSL toolkit and library on your Mac, you must open the Terminal application, go to the OpenSSL source folder, and follow the instructions from the INSTALL file included in the archive.
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FixMyCert
fixmycert.com › guides › openssl-installation
Install OpenSSL: Windows, Linux, macOS, Alpine
How to install OpenSSL on Windows, Linux, macOS, and Alpine. Check if OpenSSL is pre-installed, understand LibreSSL vs OpenSSL, with copy-paste commands.
🌐
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 - When an app wants to use a library, macOS searches several locations to find it. 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.
🌐
MacPorts
ports.macports.org › port › openssl3
Install openssl3 on macOS with MacPorts
To install openssl3, run the following command in macOS terminal (Applications->Utilities->Terminal)