TIL: Running Rails 5 / Ruby 2 on Ubuntu 2022.4

I saw an article that Ubuntu 2022.10 had been released, which spurred me to finally upgrade my Dell laptop from 2018.4 to 2022.4 Everything went great!… until I went to write some code. With the upgrade, rvm needed to be reinstalled. With that, I went to the rvm website, saw there is now an ubuntu repository, and installed without an issue. I then ran rvm install "ruby-2.5.3", which failed during compile:

Error running '__rvm_make -j8'

The interwebs pointed to the issue being OpenSSL. In the make log, about 250 lines before the end, I found the issue which confirmed that:

ossl.c:63:1: note: in expansion of macro ‘OSSL_IMPL_ARY2SK’
   63 | OSSL_IMPL_ARY2SK(x509, X509, cX509Cert, DupX509CertPtr)
      | ^~~~~~~~~~~~~~~~
ossl.c: In function ‘ossl_clear_error’:
ossl.c:311:9: error: ‘ERR_get_error_line_data’ is deprecated: Since OpenSSL 3.0 [-Werror=deprecated-declarations]

I tried several fixes:

• Install openssl via rvm pkg install openssl and then install ruby pointing to that package: This *almost* worked. Ruby and Rails installed and the server launched… and then would core dump as soon as you sent a request to the server.
• See there’s an open PR to fix this in RVM for certain versions and curse the fates.
• Try tweaking my versions of ruby required… but I needed to then get to Ruby 3.1 and Rails 5.3 only supports up to Ruby 2.7 so no luck there.
• Notice rvm has patchsets for Ruby 2.5.1 that mention openssl, so try downgrading, but I received the same error.

Finally, at around midnight I finally found an article on AskUbuntu about OpenSSL and the following answer:

After a few tweaks (I also had to load the dev package) I was able to install OpenSSL 1.1.1:

wget http://security.ubuntu.com/ubuntu/pool/main/o/openssl/libssl1.1_1.1.1f-1ubuntu2.16_amd64.deb
wget http://security.ubuntu.com/ubuntu/pool/main/o/openssl/libssl-dev_1.1.1f-1ubuntu2.16_amd64.deb
sudo dpkg -i libssl1.1_1.1.1f-1ubuntu2.16_amd64.deb 
sudo dpkg -i libssl-dev_1.1.1f-1ubuntu2.16_amd64.deb

With that, I was finally able to successfully install Ruby, and have a working dev instance again!