Gem Eventmachine Fatal Error: 'Openssl/Ssl.H' File Not Found

gem eventmachine fatal error: 'openssl/ssl.h' file not found

$ gem install eventmachine -- --with-cppflags=-I/usr/local/opt/openssl/include                                                                                                             
Building native extensions with: '--with-cppflags=-I/usr/local/opt/openssl/include'
This could take a while...
Successfully installed eventmachine-1.0.8
1 gem installed

You can also set up bundler like this but I think that is superficial

bundle config build.eventmachine --with-cppflags=-I/usr/local/opt/openssl/include

Can't install middleman due to gem install failure

It looks like it's an issue with El Capitan not providing openSSL headers.

https://github.com/eventmachine/eventmachine/issues/643

The solution is to install openssl using Homebrew or MacPorts brew install openssl

I had to do brew link openssl --force as openSSL was already installed

Error 'openssl/crypto.h' file not found when installing PycURL on Mac using pip

What eventually helped was:

1. Remove pycurl from the requirements.txt file
2. Install openssl with: brew install openssl
3. Find openssl installation directory with

$ brew --prefix openssl
/usr/local/opt/openssl@3

$ ls -la /usr/local/opt/openssl@3
lrwxr-xr-x  1 runner  admin  25 Jul  6 09:13 /usr/local/opt/openssl@3 -> ../Cellar/openssl@3/3.0.4

4. Install PycURL specifying inline the above openssl install directories like this:

PYCURL_SSL_LIBRARY=openssl LDFLAGS="-L/usr/local/Cellar/openssl@3/3.0.4/lib" CPPFLAGS="-I/usr/local/Cellar/openssl@3/3.0.4/include" pip3 install --no-cache-dir pycurl

5. Now the PycURL installs without any problem:

Collecting pycurl
  Downloading pycurl-7.45.1.tar.gz (233 kB)
     ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ 233.9/233.9 kB 64.5 MB/s eta 0:00:00
  Preparing metadata (setup.py): started
  Preparing metadata (setup.py): finished with status 'done'
Building wheels for collected packages: pycurl
  Building wheel for pycurl (setup.py): started
  Building wheel for pycurl (setup.py): finished with status 'done'
  Created wheel for pycurl: filename=pycurl-7.45.1-cp39-cp39-macosx_10_15_x86_64.whl size=146607 sha256=aff9581cbd6ddec739c529df376ad2d4edf49dafdad179a9b68bddeb60a739b3
  Stored in directory: /private/var/folders/24/8k48jl6d249_n_qfxwsl6xvm0000gn/T/pip-ephem-wheel-cache-hjqadgim/wheels/4d/ef/77/ffab9dc4b0016ce4f780b752e0020815e416f0d27a701a816f
Successfully built pycurl
Installing collected packages: pycurl
Successfully installed pycurl-7.45.1

fatal error: openssl/ssl.h: No such file or directory

It looks like that the development package for openssl is not installed:

https://stackoverflow.com/a/3016986/5147260

openssl/ssl.h not found but installed with homebrew

I found the solution: clang was not looking in the right place.

xcode-select --install

This post resolved this issue: On mac, g++ (clang) fails to search /usr/local/include and /usr/local/lib by default

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