Can't install Jekyll - "fatal error: 'openssl/ssl.h' file not found"

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1

I am attempting to locally host a Jekyll site on Mac OS.
Upon downloading Jekyll with gem install jekyll I am met with error:

current directory: /Users/main/.rvm/gems/ruby-3.0.0/gems/eventmachine-1.2.7/ext
make DESTDIR\= sitearchdir\=./.gem.20221106-46436-a98sx9 sitelibdir\=./.gem.20221106-46436-a98sx9
compiling binder.cpp
In file included from binder.cpp:20:
./project.h:119:10: fatal error: 'openssl/ssl.h' file not found
#include <openssl/ssl.h>
         ^~~~~~~~~~~~~~~
1 error generated.
make: *** [binder.o] Error 1

make failed, exit code 2

I am on MacOS Ventura 13.0.

  • openssl version returns LibreSSL 3.3.6

  • jekyll -v returns can't find gem jekyll (>= 0.a) with executable jekyll (Gem::GemNotFoundException) (obviously)

  • ruby -v returns ruby 3.0.0p0 (2020-12-25 revision 95aff21468) [x86_64-darwin22]

  • gem -v returns 3.3.25

  • bundle -v returns Bundler version 2.3.25

  • rvm list returns =* ruby-3.0.0 [ x86_64 ]

  • gem list returns

rubygems-bundler (1.4.5)
rubygems-update (3.3.25, 3.0.0)
rvm (1.11.3.9)

… among other things. No Ruby version is listed.

I have attempted brew link --force openssl , so that I can run gem install event machine (with flags), but brew link --force openssl returns

If you need to have openssl@3 first in your PATH, run:
  echo 'export PATH="/usr/local/opt/openssl@3/bin:$PATH"' >> ~/.zshrc

I ran that command, re-ran brew link --force openssl, and it returned the same error.

What do I do?
Thank you for any help.

2

Do you have the perquisites installed?

Also I created this video that shows how to install Jekyll on a Mac (it says Apple Silicon but works on Intel Macs as well):

Or if you don’t want to deal with installing Ruby and putting all this code on your computer, you can use Docker containers which is what I do on my Mac nowadays:

4

I’ve also been unable to get things re-installed with MacOS Ventura 13.0.1

I’ve been going through the install steps here: https://jekyllrb.com/docs/installation/macos/

And when I do: ruby-install ruby
I get this error:

compiling variable.c

./tool/file2lastrev.rb:6:in `require’: cannot load such file – optparse (LoadError)

from ./tool/file2lastrev.rb:6:in `’

make: *** [revision.tmp] Error 1

!!! Compiling ruby 3.1.2 failed!

5

Honestly, I gave up messing with it. I’m using the Docker method and it works perfectly. I’d go that route if I had to deal with this again.
Gl :slight_smile:

6

try uninstalling ruby and re-install it. I think macs have a built in/system version of ruby and seems to have conflicts of some sort.

7

my best solution, easy, and it works for all citizens of the world.

Go and get windows computer.

8

Now now @ninja. No need to go there.

9

I think @rdyar is on the right track. Look at this thread, which shows how to uninstall and re-install Ruby.

macOS comes with a version of Ruby installed that [I guess??] Apple uses and is locked down. That is what makes things a little more complicated.

Hopefully, this resolves the issue!

10

There seems to be some sort of conflict between MacOS 13 and Xcode 14.

This post says that there is a fix in Ruby 3.1.3 but when I do rbenv install 3.1.3 I get this error:

Installing ruby-3.1.3...
ruby-build: using readline from homebrew

BUILD FAILED (macOS 13.1 using ruby-build 20221225)

Inspect or clean up the working tree at /var/folders/cn/ws27369s34z4503m3qxqbr780000gn/T/ruby-build.20221228130313.48649.DBSkdk
Results logged to /var/folders/cn/ws27369s34z4503m3qxqbr780000gn/T/ruby-build.20221228130313.48649.log

Last 10 log lines:
compiling dln.c
compiling localeinit.c
compiling array.c
compiling mjit.c
./tool/file2lastrev.rb:6:in `require': cannot load such file -- optparse (LoadError)
	from ./tool/file2lastrev.rb:6:in `<main>'
make: *** [revision.tmp] Error 1
make: *** Waiting for unfinished jobs....
/bin/sh ./tool/ifchange "--timestamp=.rbconfig.time" rbconfig.rb rbconfig.tmp
rbconfig.rb updated