I love rvm but won't pretend that I don't have to fight with it to stay on the latest version of Ruby when using my mac.

Here's an example that popped up when trying to work with the new WriteBooks codebase that was released the past week by the Basecamp team.

danbradbury•Documents/Github/writebook» rvm install "ruby-3.3.1"                                                                                                                                                                     [16:36:02]
ruby-3.3.1 - #removing src/ruby-3.3.1 - please wait
Searching for binary rubies, this might take some time.
No binary rubies available for: osx/14.4/arm64/ruby-3.3.1.
Continuing with compilation. Please read 'rvm help mount' to get more information on binary rubies.
Checking requirements for osx.
Certificates bundle '/opt/homebrew/etc/openssl@1.1/cert.pem' is already up to date.
Requirements installation successful.
Installing Ruby from source to: /Users/danbradbury/.rvm/rubies/ruby-3.3.1, this may take a while depending on your cpu(s)...
ruby-3.3.1 - #downloading ruby-3.3.1, this may take a while depending on your connection...
ruby-3.3.1 - #extracting ruby-3.3.1 to /Users/danbradbury/.rvm/src/ruby-3.3.1 - please wait
ruby-3.3.1 - #configuring - please wait
ruby-3.3.1 - #post-configuration - please wait
ruby-3.3.1 - #compiling - please wait
Error running '__rvm_make -j8',
please read /Users/danbradbury/.rvm/log/1720136164_ruby-3.3.1/make.log

There has been an error while running make. Halting the installation.

Looking at the log file that is referenced we see errors liks this..

compiling ossl_cipher.c
compiling eventids1.c
In file included from ossl_bio.c:10:
In file included from ./ossl.h:175:
./openssl_missing.h:195:11: warning: 'TS_VERIFY_CTS_set_certs' macro redefined [-Wmacro-redefined]
#  define TS_VERIFY_CTS_set_certs(ctx, crts) ((ctx)->certs=(crts))
          ^
/opt/homebrew/Cellar/openssl@3/3.3.0/include/openssl/ts.h:426:11: note: previous definition is here
#  define TS_VERIFY_CTS_set_certs(ctx, cert) TS_VERIFY_CTX_set_certs(ctx,cert)
          ^
1 warning generated.
In file included from ossl_bn.c:11:
In file included from ./ossl.h:175:
./openssl_missing.h:195:11: warning: 'TS_VERIFY_CTS_set_certs' macro redefined [-Wmacro-redefined]
#  define TS_VERIFY_CTS_set_certs(ctx, crts) ((ctx)->certs=(crts))
          ^
/opt/homebrew/Cellar/openssl@3/3.3.0/include/openssl/ts.h:426:11: note: previous definition is here
#  define TS_VERIFY_CTS_set_certs(ctx, cert) TS_VERIFY_CTX_set_certs(ctx,cert)
          ^

For those who know SSL is a pain in the ass on Mac and you will need to pass additional arguments to get the compilation to work correctly.. TS_VERIFY_CTS_set_certs was removed in the latest version of OpenSSL (3 is current). To combat this we need to run the following and use the 1.x version we have on our machine

rvm install "ruby-3.3.1" --with-openssl-dir=$(brew --prefix openssl@1.1)

For those curious and not familiar with the underlying brew usage all we are doing is using prefix to give us the path in which Homebrew installed the package (man brew)

I'm sure there's other gotchas on machines that aren't setup with Ruby already but that's an annoying one that I almost always forget about.