Homebrew refusing to link OpenSSL - macos

I'm on: OSX 10.11.6, Homebrew version 0.9.9m OpenSSL 0.9.8zg 14 July 2015
I'm trying to play with with dotnetcore and by following their instructions,
I've upgraded/installed the latest version of openssl:
> brew install openssl
==> Downloading https://homebrew.bintray.com/bottles/openssl-1.0.2h_1.el_capitan.bottle.tar.gz
Already downloaded: /Users/administrator/Library/Caches/Homebrew/openssl-1.0.2h_1.el_capitan.bottle.tar.gz
==> Pouring openssl-1.0.2h_1.el_capitan.bottle.tar.gz
==> Caveats
A CA file has been bootstrapped using certificates from the system
keychain. To add additional certificates, place .pem files in
/usr/local/etc/openssl/certs
and run
/usr/local/opt/openssl/bin/c_rehash
This formula is keg-only, which means it was not symlinked into /usr/local.
Apple has deprecated use of OpenSSL in favor of its own TLS and crypto libraries
Generally there are no consequences of this for you. If you build your
own software and it requires this formula, you'll need to add to your
build variables:
LDFLAGS: -L/usr/local/opt/openssl/lib
CPPFLAGS: -I/usr/local/opt/openssl/include
But when I try to link openssl I continue to run into this linking error:
> brew link --force openssl
Warning: Refusing to link: openssl
Linking keg-only OpenSSL means you may end up linking against the insecure,
deprecated system version while using the headers from the Homebrew version.
Instead, pass the full include/library paths to your compiler e.g.:
-I/usr/local/opt/openssl/include -L/usr/local/opt/openssl/lib
The option to include compiler flags doesn't make sense to me, since I'm not compiling these libraries that I'm dependent on.
EDIT dotnetcore has updated their instructions:
brew update
brew install openssl
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/

This is what worked for me:
brew update
brew install openssl
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/
ln -s /usr/local/Cellar/openssl/1.0.2j/bin/openssl /usr/local/bin/openssl
Thanks to #dorlandode on this thread https://github.com/Homebrew/brew/pull/597
NB: I only used this as a temporary fix until I could spend time correctly installing Openssl again from scratch. As I remember I spent best part of a day debugging and having issues before I realised the best way was to manually install the certs I needed one by one. Please read the link in #bouke's comment before attempting this.

As the update to the other answer suggests, the workaround of installing the old openssl101 brew will no longer work. For a right-now workaround, see this comment on dotnet/cli#3964.
The most relevant part of the issue copied here:
I looked into the other option that was suggested for setting the rpath on the library. I think the following is a better solution that will only effect this specific library.
sudo install_name_tool -add_rpath /usr/local/opt/openssl/lib /usr/local/share/dotnet/shared/Microsoft.NETCore.App/1.0.0/System.Security.Cryptography.Native.dylib
and/or if you have NETCore 1.0.1 installed perform the same command for 1.0.1 as well:
sudo install_name_tool -add_rpath /usr/local/opt/openssl/lib /usr/local/share/dotnet/shared/Microsoft.NETCore.App/1.0.1/System.Security.Cryptography.Native.dylib
In effect, rather than telling the operating system to always use the homebrew version of SSL and potentially causing something to break, we're telling dotnet how to find the correct library.
Also importantly, it looks like Microsoft are aware of the issue and and have both a) a somewhat immediate plan to mitigate as well as b) a long-term solution (probaby bundling OpenSSL with dotnet).
Another thing to note: /usr/local/opt/openssl/lib is where the brew is linked by default:
13:22 $ ls -l /usr/local/opt/openssl
lrwxr-xr-x 1 ben admin 26 May 15 14:22 /usr/local/opt/openssl -> ../Cellar/openssl/1.0.2h_1
If for whatever reason you install the brew and link it in a different location, then that path is the one you should use as an rpath.
Once you've update the rpath of the System.Security.Cryptography.Native.dylib libray, you'll need to restart your interactive session (i.e., close your console and start another one).

None of these solutions worked for me on OS X El Capitan 10.11.6. Probably because OS X has a native version of openssl that it believes is superior, and as such, does not like tampering.
So, I took the high road and started fresh...
Manually install and symlink
cd /usr/local/src
If you're getting "No such file or directory", make it:
cd /usr/local && mkdir src && cd src
Download openssl:
curl --remote-name https://www.openssl.org/source/openssl-1.0.2h.tar.gz
Extract and cd in:
tar -xzvf openssl-1.0.2h.tar.gz
cd openssl-1.0.2h
Compile and install:
./configure darwin64-x86_64-cc --prefix=/usr/local/openssl-1.0.2h shared
make depend
make
make install
Now symlink OS X's openssl to your new and updated openssl:
ln -s /usr/local/openssl-1.0.2h/bin/openssl /usr/local/bin/openssl
Close terminal, open a new session, and verify OS X is using your new openssl:
openssl version -a

Just execute brew info openssland read the information where it says:
If you need to have this software first in your PATH run: echo 'export PATH="/usr/local/opt/openssl/bin:$PATH"' >> ~/.bash_profile

If migrating your mac breaks homebrew:
I migrated my mac, and it unlinked all my homebrew installs - including OpenSSL. This broke gem install, which is how I first noticed the problem and started trying to repair this.
After a million solutions (when migrating to OSX Sierra - 10.12.5), the solution ended up being comically simple:
brew reinstall ruby
brew reinstall openssl
Edit much later: as Gal Bracha noted in the comments, you ?might? need to delete /usr/local/opt/openssl before doing the reinstalls, just to be safe. I didn't need to at the time, but if you're still having trouble, give that a try.

After trying everything I could find and nothing worked, I just tried this:
touch ~/.bash_profile; open ~/.bash_profile
Inside the file added this line.
export PATH="$PATH:/usr/local/Cellar/openssl/1.0.2j/bin/openssl"
now it works :)
Jorns-iMac:~ jorn$ openssl version -a
OpenSSL 1.0.2j 26 Sep 2016
built on: reproducible build, date unspecified
//blah blah
OPENSSLDIR: "/usr/local/etc/openssl"
Jorns-iMac:~ jorn$ which openssl
/usr/local/opt/openssl/bin/openssl

The solution above from edwardthesecond worked for me too on Sierra
brew install openssl
cd /usr/local/include
ln -s ../opt/openssl/include/openssl
./configure && make
Other steps I did before were:
installing openssl via brew
brew install openssl
adding openssl to the path as suggested by homebrew
brew info openssl
echo 'export PATH="/usr/local/opt/openssl/bin:$PATH"' >> ~/.bash_profile

I have a similar case. I need to install openssl via brew and then use pip to install mitmproxy. I get the same complaint from brew link --force. Following is the solution I reached: (without force link by brew)
LDFLAGS=-L/usr/local/opt/openssl/lib
CPPFLAGS=-I/usr/local/opt/openssl/include
PKG_CONFIG_PATH=/usr/local/opt/openssl/lib/pkgconfig
pip install mitmproxy
This does not address the question straightforwardly. I leave the one-liner in case anyone uses pip and requires the openssl lib.
Note: the /usr/local/opt/openssl/lib paths are obtained by brew info openssl

This worked for me:
brew install openssl
cd /usr/local/include
ln -s ../opt/openssl/include/openssl .

By default, homebrew gave me OpenSSL version 1.1 and I was looking for version 1.0 instead. This worked for me.
To install version 1.0:
brew install https://github.com/tebelorg/Tump/releases/download/v1.0.0/openssl.rb
Then I tried to symlink my way through it but it gave me the following error:
ln -s /usr/local/Cellar/openssl/1.0.2t/include/openssl /usr/bin/openssl
ln: /usr/bin/openssl: Operation not permitted
Finally linked openssl to point to 1.0 version using brew switch command:
brew switch openssl 1.0.2t
Cleaning /usr/local/Cellar/openssl/1.0.2t
Opt link created for /usr/local/Cellar/openssl/1.0.2t

I had the same problem while trying to install newer version of ruby 2.6.5
https://github.com/kelaberetiv/TagUI/issues/86 helps me to solve the problem. This if for macOS catalina Version 10.15.1
Basically, I did update and upgrade homebrew and install openssl and install ruby.
brew update && brew upgrade
brew install openssl
Then create these 2 symlinks
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/
then installed ruby 2.6.5

Note: this no longer works due to https://github.com/Homebrew/brew/pull/612
I had the same problem today. I uninstalled (unbrewed??) openssl 1.0.2 and installed 1.0.1 also with homebrew. Dotnet new/restore/run then worked fine.
Install openssl 101:
brew install homebrew/versions/openssl101
Linking:
brew link --force homebrew/versions/openssl101

for me this is what worked...
I edited the ./bash_profile and added below command
export PATH="/usr/local/opt/openssl/bin:$PATH"

export https_proxy=http://127.0.0.1:1087 http_proxy=http://127.0.0.1:1087 all_proxy=socks5://127.0.0.1:1080
works for me
and I think it can solve all the problems like
Failed to connect to raw.githubusercontent.com port 443: Connection refused

The solution might be updating some tools.
Here's my scenario from 2020 with Ruby and Python:
I needed to install Python 3 on Mac and things escalated. In the end, updating homebrew, node and python lead to the problem with openssl. I did not have openssl 1.0 anymore, so I couldn't "brew switch" to it.
So what was still trying to use that old 1.0 version?
It tuned out it was Ruby 2.5.5.
So I just installed Ruby 2.5.8 and removed the old one.
Other things you can try if this is not enough: Use rbenv and pyenv. Clean up gems and formulas. Update homebrew, node, yarn. Upgrade bundler. Make sure your .bash_profile (or equivalent) is set up according to each tool's instructions. Reopen the terminal.

Related

OpenSSL 1.0.2m on macOS

For building one particular library I need openssl library version 1.0.2m with devel package. I am working on macOS. Using brew install openssl installs latest version 1.1.1d.
Since OpenSSL 1.0.2 is end of lifed by the end of 2019, it is no longer available via Homebrew. This is mentioned in the Homebrew 2.2.0 announcement.
It is fairly straightforward to build and install OpenSSL 1.0.2 yourself from source. You can download your required version from the Old 1.0.2 Releases page and follow the instructions found in INSTALL.
It may be possible as well to recover an older formula and install from that, but I can not guarantee how well that works. The following steps did complete the installation process:
$ git clone https://github.com/Homebrew/homebrew-core.git
$ cd homebrew-core
$ git checkout 75b57384 Formula/openssl.rb
$ brew install Formula/openssl.rb
For me, this showed:
Warning: openssl 1.1.1d is available and more recent than version 1.0.2m.
==> Downloading https://homebrew.bintray.com/bottles/openssl-1.0.2m.high_sierra.bottle.tar.gz
and went on happily after that. A quick try at the end gives some confidence that it worked out well:
$ /usr/local/opt/openssl/bin/openssl version
OpenSSL 1.0.2m 2 Nov 2017
If you prefer not to use git directly, you can also try downloading that version of openssl.rb from gitHub.com and run brew install on it.
If you wonder where that commit hash came from, I happened to know that the formula used to be called -- surprise -- openssl.rb (but using git to query for removed files would have worked as well). Therefore, I inspected the history for Formula/openssl.rb and found:
$ git log -- Formula/openssl.rb
...
commit 75b573845a17aaf3f7c84dc58e97cf5fe39a502b
Author: BrewTestBot <brew-test-bot#googlegroups.com>
Date: Thu Nov 2 17:20:33 2017 +0000
openssl: update 1.0.2m bottle.
Recently I was struggling due to the recent update in openssl version from 1.0 to 1.1 and wanted to revert it back to older version. No other solution except the one given below worked for me:
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
Instead of downloading the specific version of Formula/openssl.rb you can just use the raw reference to the file with the specific commit SHA as mentioned here.
So for the last update to version 1.0.2t the SHA is 8b9d6d688f483a0f33fcfc93d433de501b9c3513
commit 8b9d6d688f483a0f33fcfc93d433de501b9c3513
Author: BrewTestBot <homebrew-test-bot#lists.sfconservancy.org>
Date: Sat Sep 28 19:38:49 2019 +0000
openssl: update 1.0.2t bottle.
So I would execute the following command to install 1.0.2t.
brew install https://raw.githubusercontent.com/Homebrew/homebrew-core/8b9d6d688f483a0f33fcfc93d433de501b9c3513/Formula/openssl.rb
1- Download the file:
wget https://github.com/tebelorg/Tump/releases/download/v1.0.0/openssl.rb
2 - Run brew with the file downloaded:
brew install openssl.rb
Other solutions won't work because you will get this error "Calling Installation of openssl from a GitHub commit URL is disabled! Use 'brew extract openssl' to stable tap on GitHub instead." the following steps will fix it:
First go to the local installation of homebrew
cd /usr/local/Homebrew/
Homebrew 2.5 remove the option to install formulas directly from git repos so we need to checkout an older version
git checkout 2.3.0
Install openssl latest 1.0.x version
HOMEBREW_NO_AUTO_UPDATE=1 brew install https://github.com/tebelorg/Tump/releases/download/v1.0.0/openssl.rb
Go back to current version of homebrew
git co -
Tell brew to use the old version of openssl this way you can chose wich version to use if you have both intalled
brew switch openssl 1.0.2t
Update - I think I've been getting downvotes because I've simply posted a link without the solution. So here's the solution:
Download this formula for OpenSSL V1.0 (It is patched to work with the arm64 processor)
Install it brew install openssl#1.0.rb
Add this version to the beginning of your PATH.
Note: Make sure that RVM is the last PATH variable change in your shell config file (.zshrc / .bashrc)
echo 'export PATH="/opt/homebrew/opt/openssl#1.0/bin:$PATH"' >> ~/.zshrc
Export some required environment variables
export LDFLAGS="-L/opt/homebrew/opt/openssl#1.0/lib"
export CPPFLAGS="-I/opt/homebrew/opt/openssl#1.0/include"
export PKG_CONFIG_PATH="/opt/homebrew/opt/openssl#1.0/lib/pkgconfig"
Reload your shell config source ~/.zshrc
Verify your openssl version
> openssl version
OpenSSL 1.0.2u 20 Dec 2019
Disable RVM autolibs rvm autolibs disable
Export some env variables to avoid compilation errors
export RUBY_CFLAGS=-DUSE_FFI_CLOSURE_ALLOC
export optflags="-Wno-error=implicit-function-declaration"
Install Ruby
rvm install 2.3.0 --with-openssl-dir=/opt/homebrew/opt/openssl#1.0
Ref
Maybe it's not a perfect idea, but it solved my problem (libssl.1.0.0.dylib image not found):
sudo ln -s /usr/lib/libssl.dylib /usr/local/opt/openssl/lib/libssl.1.0.0.dylib
sudo ln -s /usr/lib/libcrypto.dylib /usr/local/opt/openssl/lib/libcrypto.1.0.0.dylib
Hope it works for you!
See this reply
Here is the linux-brew formula for openssl#1.0.2
brew install https://raw.githubusercontent.com/Homebrew/linuxbrew-core/20ab55b304597c6c47149dc0e50bd5f7ea45b678/Formula/openssl.rb

Homebrew refusing to link OpenSSL on OS X 10.12 [duplicate]

I'm on: OSX 10.11.6, Homebrew version 0.9.9m OpenSSL 0.9.8zg 14 July 2015
I'm trying to play with with dotnetcore and by following their instructions,
I've upgraded/installed the latest version of openssl:
> brew install openssl
==> Downloading https://homebrew.bintray.com/bottles/openssl-1.0.2h_1.el_capitan.bottle.tar.gz
Already downloaded: /Users/administrator/Library/Caches/Homebrew/openssl-1.0.2h_1.el_capitan.bottle.tar.gz
==> Pouring openssl-1.0.2h_1.el_capitan.bottle.tar.gz
==> Caveats
A CA file has been bootstrapped using certificates from the system
keychain. To add additional certificates, place .pem files in
/usr/local/etc/openssl/certs
and run
/usr/local/opt/openssl/bin/c_rehash
This formula is keg-only, which means it was not symlinked into /usr/local.
Apple has deprecated use of OpenSSL in favor of its own TLS and crypto libraries
Generally there are no consequences of this for you. If you build your
own software and it requires this formula, you'll need to add to your
build variables:
LDFLAGS: -L/usr/local/opt/openssl/lib
CPPFLAGS: -I/usr/local/opt/openssl/include
But when I try to link openssl I continue to run into this linking error:
> brew link --force openssl
Warning: Refusing to link: openssl
Linking keg-only OpenSSL means you may end up linking against the insecure,
deprecated system version while using the headers from the Homebrew version.
Instead, pass the full include/library paths to your compiler e.g.:
-I/usr/local/opt/openssl/include -L/usr/local/opt/openssl/lib
The option to include compiler flags doesn't make sense to me, since I'm not compiling these libraries that I'm dependent on.
EDIT dotnetcore has updated their instructions:
brew update
brew install openssl
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/
This is what worked for me:
brew update
brew install openssl
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/
ln -s /usr/local/Cellar/openssl/1.0.2j/bin/openssl /usr/local/bin/openssl
Thanks to #dorlandode on this thread https://github.com/Homebrew/brew/pull/597
NB: I only used this as a temporary fix until I could spend time correctly installing Openssl again from scratch. As I remember I spent best part of a day debugging and having issues before I realised the best way was to manually install the certs I needed one by one. Please read the link in #bouke's comment before attempting this.
As the update to the other answer suggests, the workaround of installing the old openssl101 brew will no longer work. For a right-now workaround, see this comment on dotnet/cli#3964.
The most relevant part of the issue copied here:
I looked into the other option that was suggested for setting the rpath on the library. I think the following is a better solution that will only effect this specific library.
sudo install_name_tool -add_rpath /usr/local/opt/openssl/lib /usr/local/share/dotnet/shared/Microsoft.NETCore.App/1.0.0/System.Security.Cryptography.Native.dylib
and/or if you have NETCore 1.0.1 installed perform the same command for 1.0.1 as well:
sudo install_name_tool -add_rpath /usr/local/opt/openssl/lib /usr/local/share/dotnet/shared/Microsoft.NETCore.App/1.0.1/System.Security.Cryptography.Native.dylib
In effect, rather than telling the operating system to always use the homebrew version of SSL and potentially causing something to break, we're telling dotnet how to find the correct library.
Also importantly, it looks like Microsoft are aware of the issue and and have both a) a somewhat immediate plan to mitigate as well as b) a long-term solution (probaby bundling OpenSSL with dotnet).
Another thing to note: /usr/local/opt/openssl/lib is where the brew is linked by default:
13:22 $ ls -l /usr/local/opt/openssl
lrwxr-xr-x 1 ben admin 26 May 15 14:22 /usr/local/opt/openssl -> ../Cellar/openssl/1.0.2h_1
If for whatever reason you install the brew and link it in a different location, then that path is the one you should use as an rpath.
Once you've update the rpath of the System.Security.Cryptography.Native.dylib libray, you'll need to restart your interactive session (i.e., close your console and start another one).
None of these solutions worked for me on OS X El Capitan 10.11.6. Probably because OS X has a native version of openssl that it believes is superior, and as such, does not like tampering.
So, I took the high road and started fresh...
Manually install and symlink
cd /usr/local/src
If you're getting "No such file or directory", make it:
cd /usr/local && mkdir src && cd src
Download openssl:
curl --remote-name https://www.openssl.org/source/openssl-1.0.2h.tar.gz
Extract and cd in:
tar -xzvf openssl-1.0.2h.tar.gz
cd openssl-1.0.2h
Compile and install:
./configure darwin64-x86_64-cc --prefix=/usr/local/openssl-1.0.2h shared
make depend
make
make install
Now symlink OS X's openssl to your new and updated openssl:
ln -s /usr/local/openssl-1.0.2h/bin/openssl /usr/local/bin/openssl
Close terminal, open a new session, and verify OS X is using your new openssl:
openssl version -a
Just execute brew info openssland read the information where it says:
If you need to have this software first in your PATH run: echo 'export PATH="/usr/local/opt/openssl/bin:$PATH"' >> ~/.bash_profile
If migrating your mac breaks homebrew:
I migrated my mac, and it unlinked all my homebrew installs - including OpenSSL. This broke gem install, which is how I first noticed the problem and started trying to repair this.
After a million solutions (when migrating to OSX Sierra - 10.12.5), the solution ended up being comically simple:
brew reinstall ruby
brew reinstall openssl
Edit much later: as Gal Bracha noted in the comments, you ?might? need to delete /usr/local/opt/openssl before doing the reinstalls, just to be safe. I didn't need to at the time, but if you're still having trouble, give that a try.
After trying everything I could find and nothing worked, I just tried this:
touch ~/.bash_profile; open ~/.bash_profile
Inside the file added this line.
export PATH="$PATH:/usr/local/Cellar/openssl/1.0.2j/bin/openssl"
now it works :)
Jorns-iMac:~ jorn$ openssl version -a
OpenSSL 1.0.2j 26 Sep 2016
built on: reproducible build, date unspecified
//blah blah
OPENSSLDIR: "/usr/local/etc/openssl"
Jorns-iMac:~ jorn$ which openssl
/usr/local/opt/openssl/bin/openssl
The solution above from edwardthesecond worked for me too on Sierra
brew install openssl
cd /usr/local/include
ln -s ../opt/openssl/include/openssl
./configure && make
Other steps I did before were:
installing openssl via brew
brew install openssl
adding openssl to the path as suggested by homebrew
brew info openssl
echo 'export PATH="/usr/local/opt/openssl/bin:$PATH"' >> ~/.bash_profile
I have a similar case. I need to install openssl via brew and then use pip to install mitmproxy. I get the same complaint from brew link --force. Following is the solution I reached: (without force link by brew)
LDFLAGS=-L/usr/local/opt/openssl/lib
CPPFLAGS=-I/usr/local/opt/openssl/include
PKG_CONFIG_PATH=/usr/local/opt/openssl/lib/pkgconfig
pip install mitmproxy
This does not address the question straightforwardly. I leave the one-liner in case anyone uses pip and requires the openssl lib.
Note: the /usr/local/opt/openssl/lib paths are obtained by brew info openssl
This worked for me:
brew install openssl
cd /usr/local/include
ln -s ../opt/openssl/include/openssl .
By default, homebrew gave me OpenSSL version 1.1 and I was looking for version 1.0 instead. This worked for me.
To install version 1.0:
brew install https://github.com/tebelorg/Tump/releases/download/v1.0.0/openssl.rb
Then I tried to symlink my way through it but it gave me the following error:
ln -s /usr/local/Cellar/openssl/1.0.2t/include/openssl /usr/bin/openssl
ln: /usr/bin/openssl: Operation not permitted
Finally linked openssl to point to 1.0 version using brew switch command:
brew switch openssl 1.0.2t
Cleaning /usr/local/Cellar/openssl/1.0.2t
Opt link created for /usr/local/Cellar/openssl/1.0.2t
I had the same problem while trying to install newer version of ruby 2.6.5
https://github.com/kelaberetiv/TagUI/issues/86 helps me to solve the problem. This if for macOS catalina Version 10.15.1
Basically, I did update and upgrade homebrew and install openssl and install ruby.
brew update && brew upgrade
brew install openssl
Then create these 2 symlinks
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/
then installed ruby 2.6.5
Note: this no longer works due to https://github.com/Homebrew/brew/pull/612
I had the same problem today. I uninstalled (unbrewed??) openssl 1.0.2 and installed 1.0.1 also with homebrew. Dotnet new/restore/run then worked fine.
Install openssl 101:
brew install homebrew/versions/openssl101
Linking:
brew link --force homebrew/versions/openssl101
for me this is what worked...
I edited the ./bash_profile and added below command
export PATH="/usr/local/opt/openssl/bin:$PATH"
export https_proxy=http://127.0.0.1:1087 http_proxy=http://127.0.0.1:1087 all_proxy=socks5://127.0.0.1:1080
works for me
and I think it can solve all the problems like
Failed to connect to raw.githubusercontent.com port 443: Connection refused
The solution might be updating some tools.
Here's my scenario from 2020 with Ruby and Python:
I needed to install Python 3 on Mac and things escalated. In the end, updating homebrew, node and python lead to the problem with openssl. I did not have openssl 1.0 anymore, so I couldn't "brew switch" to it.
So what was still trying to use that old 1.0 version?
It tuned out it was Ruby 2.5.5.
So I just installed Ruby 2.5.8 and removed the old one.
Other things you can try if this is not enough: Use rbenv and pyenv. Clean up gems and formulas. Update homebrew, node, yarn. Upgrade bundler. Make sure your .bash_profile (or equivalent) is set up according to each tool's instructions. Reopen the terminal.

Nginx Cannot Find OpenSSL Development Headers

When I run: rvmsudo passenger-install-nginx-module on my Mac to install nginx, the terminal prints:
Checking for OpenSSL development headers...
Found: no
But I am certain I have openssl installed. which openssl returns /usr/local/openssl/bin/openssl and /usr/local/openssl/bin: is the first entry in my $PATH. My questions are:
Are the OpenSSL development headers included with the regular openssl install through homebrew?
If they aren't, where should I download them from?
If brew link openssl --force gives you this message:
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. Instead, pass the full include/library paths to your compiler e.g.: -I/usr/local/opt/openssl/include -L/usr/local/opt/openssl/lib
Try this:
$ brew doctor (now fix anything that it tells you to fix)
$ brew update
$ brew upgrade
Now let's install it:
$ brew install openssl
And now we'll link it into our public area so you don't have to figure out the magic environment variable to set while building your favorite OpenSSL-backed library:
$ cd /usr/local/include
$ ln -s ../opt/openssl/include/openssl .
All done! Enjoy
If you are on Mac OS X El Capitan, Apple doesn't include openssl any more because of security problems openssl had, I have similar problem installing Passenger. brew just installs openssl itself without development headers.
If you are on an older version of Mac OS X than El Capitan, you can use:
xcode-select --install
which installs openssl development headers as well.
EDIT:
Updating brew and installing openssl and force linking openssl to brew version solved my problem:
$ brew update
$ which openssl
/usr/bin/openssl
$ brew install openssl
$ brew link openssl --force
$ which openssl
/usr/local/bin/openssl

OSX's openssl version is diffrent from brew's openssl

I just typed openssl version in terminal and I got following result:
OpenSSL 0.9.8y 5 Feb 2013
So I ran brew update and brew upgrade openssl.
Which the first one returned Updated Homebrew from 7afeb3af to 8cabfe85., And second one returned openssl-1.0.1g already installed.
So typed brew link --force openssl.
After above procedure I typed openssl version And I got the same result
OpenSSL 0.9.8y 5 Feb 2013.
How can I update openssl on mac osx 10.9.3?
Run brew info openssl and follow the instructions there. Do not try to --force link the latest openssl with the one that comes installed with OSX by default. (0.9.8)
Specifically it'll ask you to add the Homebrew version of openssl (should be 1.0.2 as of this date) into your $PATH.
echo 'export PATH="/usr/local/opt/openssl/bin:$PATH"' >> ~/.bash_profile
Note: Make sure to remove any export PATH lines from the bash_profile, since this line above exports it for you appending the rest of the $PATH variable to the end. To view the bash profile use vi ~/.bash_profile
Doing this should fix any problems with installing packages (especially Ruby Gems that need compiling).
So here's what is going on. You have two copies of OpenSSL.
Version 0.9.8 - located at /usr/bin/openssl, pre-installed on OS X
Version 1.0.1g - located at /usr/local/Cellar/openssl/1.0.1h/bin/openssl, installed by brew.
When you ran brew upgrade openssl, you actually ran brew install openssl since brew had not yet install openssl on your system. (Remember, brew doesn't control all the software on your computer - only what it installed).
Turns out that the message of brew install openssl:
==> Caveats
A CA file has been bootstrapped using certificates from the system
keychain. To add additional certificates, place .pem files in
/usr/local/etc/openssl/certs
and run
/usr/local/opt/openssl/bin/c_rehash
This formula is keg-only, so it was not symlinked into /usr/local.
Mac OS X already provides this software and installing another version in
parallel can cause all kinds of trouble.
The OpenSSL provided by OS X is too old for some software.
Generally there are no consequences of this for you. If you build your
own software and it requires this formula, you'll need to add to your
build variables:
LDFLAGS: -L/usr/local/opt/openssl/lib
CPPFLAGS: -I/usr/local/opt/openssl/include
This actually explains that OS X comes preinstalled. Using a different non-system openssl may cause issues if you change from the default openssl. Hence, brew kindly did not link it into your /usr/local which is probably part of your path.
I presume you wanted to upgrade the openssl on you box because some package you were trying to install required a newer version. Ahoy - the message tells you that you should install that software package and point it at your new shiny brew openssl.

Cannot install ruby-1.9.2 in Mac OSX 10.8.1 due to symlink error

First, I tried the common rvm install.
rvm install 1.9.2
However, the following error was shown:
The provided compiler '/usr/bin/gcc' is LLVM based, it is not yet fully supported by ruby and gems, please read `rvm requirements`.
Then I run
rvm requirements
and find these following part of output useful
Right now Ruby requires gcc to compile, but Xcode 4.2 and later no longer ship with gcc. Instead they ship with llvm-gcc (to which gcc is a symlink) and clang, neither of which are supported for building Ruby. Xcode 4.1 was the last version to ship gcc, which was /usr/bin/gcc-4.2.
Xcode 4.1 and earlier:
- Ruby will build fine.
Xcode 4.2 and later (including Command Line Tools for Xcode):
- If you have gcc-4.2 (and friends) from an earlier Xcode version, Ruby will build fine.
- If you don't have gcc-4.2, you have two options to get it:
* Install apple-gcc42 from Homebrew
* Install osx-gcc-installer
Homebrew:
If you are using Homebrew, you can install the apple-gcc42 and required libraries from homebrew/dupes:
brew update
brew tap homebrew/dupes
brew install autoconf automake apple-gcc42
rvm pkg install openssl
This can live side by side with an existing Xcode 4.2+ install or Command Line Tools for Xcode.
so I tried:
brew update
brew tap homebrew/dupes
brew install autoconf automake apple-gcc42
However, I got the following error
Warning: Could not link apple-gcc42. Unlinking...
Error: The `brew link` step did not complete successfully
The formula built, but is not symlinked into /usr/local
You can try again using `brew link apple-gcc42'
==> Summary
/usr/local/Cellar/apple-gcc42/4.2.1-5666.3: 104 files, 75M, built in 23 seconds
kanitw:shell.venturelab.com kanitw$ brew link apple-gcc42
Linking /usr/local/Cellar/apple-gcc42/4.2.1-5666.3... Warning: Could not link apple-gcc42. Unlinking...
Error: Could not symlink file: /usr/local/Cellar/apple-gcc42/4.2.1-5666.3/include/gcc
/usr/local/include is not writable. You should change its permissions.
What would be my best solution? I kinda remember from somewhere that I should not use sudo with brew since I will mess up the whole installation.
You can change /usr/local directory owner
sudo chown -R `whoami` /usr/local
But, if you have mysql installed, you mast fix its owner
sudo chown -R mysql:mysql /usr/local/mysql
You should run brew doctor and then change the permissions accordingly. There might be other issues.
Change the permissions of your /usr/local directory and try again.

Resources