Install Ruby 2.2 on Mac OSX Catalina with ruby-install - ruby

Question

Here's what I get when I try to install Ruby 2.2:
$ ruby-install ruby 2.2.10
# ...
>>> Compiling ruby 2.2.10 ...
CC = clang
LD = ld
LDSHARED = clang -dynamic -bundle
CFLAGS = -O3 -fno-fast-math -ggdb3 -Wall -Wextra -Wno-unused-parameter -Wno-parentheses -Wno-long-long -Wno-missing-field-initializers -Wunused-variable -Wpointer-arith -Wwrite-strings -Wdeclaration-after-statement -Wshorten-64-to-32 -Wimplicit-function-declaration -Wdivision-by-zero -Wdeprecated-declarations -Wextra-tokens -pipe
XCFLAGS = -D_FORTIFY_SOURCE=2 -fstack-protector -fno-strict-overflow -fvisibility=hidden -DRUBY_EXPORT -fPIE
CPPFLAGS = -I/opt/X11/include -I/usr/local/opt/openssl#1.1/include -I/usr/local/opt/readline/include -I/usr/local/opt/libyaml/include -I/usr/local/opt/gdbm/include -D_XOPEN_SOURCE -D_DARWIN_C_SOURCE -D_DARWIN_UNLIMITED_SELECT -D_REENTRANT -I. -I.ext/include/x86_64-darwin19 -I./include -I.
DLDFLAGS = -Wl,-undefined,dynamic_lookup -Wl,-multiply_defined,suppress -L/usr/local/opt/openssl#1.1/lib -L/usr/local/opt/readline/lib -L/usr/local/opt/libyaml/lib -L/usr/local/opt/gdbm/lib -fstack-protector -Wl,-u,_objc_msgSend -Wl,-pie -framework CoreFoundation
SOLIBS = -lgmp
Apple clang version 12.0.0 (clang-1200.0.31.1)
Target: x86_64-apple-darwin19.6.0
Thread model: posix
InstalledDir: /Library/Developer/CommandLineTools/usr/bin
translating probes probes.d
. ./vm_opts.h
file2lastrev.rb: does not seem to be under a vcs: .
make: [.revision.time] Error 1 (ignored)
./revision.h unchanged
compiling main.c
compiling dmydln.c
compiling miniinit.c
compiling miniprelude.c
compiling array.c
compiling bignum.c
compiling class.c
compiling compar.c
compiling complex.c
compiling dir.c
compiling dln_find.c
compiling encoding.c
encoding.c:825:2: error: implicit declaration of function 'rb_str_change_terminator_length' is invalid in C99 [-Werror,-Wimplicit-function-declaration]
rb_str_change_terminator_length(obj, oldtermlen, termlen);
^
1 error generated.
make: *** [encoding.o] Error 1
!!! Compiling ruby 2.2.10 failed!
OS Version: 10.15.6
ruby-install version: 0.7.1
Any ideas on how to debug or fix this? I was previously able to install other versions of 2.2 before I upgraded my OS. I'm also able to install later versions like Ruby 2.7 with no problem

Answer 1

After a lot of breaking my head and realizing that the error has to do with the compilation using GCC that is native to macOS, I decided to do a test.
Because older versions of Ruby need instructions that are no longer present in updated make, it is necessary to download an older version of Command Line Tools for Xcode.
First, remove your actual version with:
sudo rm -rf /Library/Developer/CommandLineTools
Ignore the error about missing git.
Proceed to https://developer.apple.com/download/more/ and download 11.x version of Command Line Tools for Xcode.
I downloaded version 11.5 and it worked.
My return when running gcc -v
Configured with: --prefix = / Library / Developer / CommandLineTools / usr --with-gxx-include-dir = / Library / Developer / CommandLineTools / SDKs / MacOSX.sdk / usr / include / c ++ / 4.2.1
Apple clang version 11.0.3 (clang-1103.0.32.62)
Target: x86_64-apple-darwin19.6.0
Thread model: posix
InstalledDir: / Library / Developer / CommandLineTools / usr / bin
To compare, with recent Command Lines, 12.x, you'll see something like:
Configured with: --prefix=/Applications/Xcode.app/Contents/Developer/usr --with-gxx-include-dir=/Applications/Xcode.app/Contents/Developer/Platforms/MacOSX.platform/Developer/SDKs/MacOSX.sdk/usr/include/c++/4.2.1
Apple clang version 12.0.0 (clang-1200.0.32.2)
Target: x86_64-apple-darwin19.6.0
Thread model: posix
InstalledDir: /Applications/Xcode.app/Contents/Developer/Toolchains/XcodeDefault.xctoolchain/usr/bin

Answer 2

Apparently ignoring the compiler warning is also an option
export optflags="-Wno-error=implicit-function-declaration"
For further duscussion see Problem when installing Ruby 2.2.9 on Mac Big Sur M1

Answer 3

I was able to install that version on Mac 10.15.7 using rvm.
I have openssl#1.1 installed with homebrew. If you run brew info openssl what do you see? I would try brew upgrade openssl first.
Try running
export PKG_CONFIG_PATH="/usr/local/opt/openssl#1.1/lib/pkgconfig" with the info brew returns. Then try rvm install 2.2.10. If that doesn't work I would try rvm install 2.2.10 --with-openssl-dir=/usr/local/opt/openssl --with-openssl-lib=/usr/local/opt/openssl/lib --with-openssl-include=/usr/local/opt/openssl/include just make sure those paths are correct for your system.
You may also need to run
export LDFLAGS="-L/usr/local/opt/openssl#1.1/lib"
export CPPFLAGS="-I/usr/local/opt/openssl#1.1/include"
beforehand, which will be supplied by brew info.

Answer 4

Adding some extra options here that might help:
We need the right SSL version:
$ brew install rbenv/tap/openssl#1.0
$ rvm install 2.2.10 -C --with-openssl-dir=`brew --prefix openssl#1.0`

Answer 5

First, install open-ssl
brew install rbenv/tap/openssl#1.0
Then
CFLAGS="-Wno-error=implicit-function-declaration" rvm reinstall ruby-2.2.5 --with-openssl-dir='/usr/local/opt/openssl#1.0'

Answer 6

I recently had to install ruby-2.2.0 in Catalina 10.15.7 and was facing the same issues. But luckily managed to get my work done. Steps are as follows:
Installed openssl as a rvm package:
$ rvm pkg install openssl
Ignored compiler warnings:
$ export optflags="-Wno-error=implicit-function-declaration"
Installed required ruby version (2.2.0 in my case) while providing openssl directory parameter and ignoring rubygems:
$ rvm install 2.2.0 --with-openssl-dir=$rvm_path/usr --rubygems ignore