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Anyone have ideas on what the issue is? The closest error message I found searching online was linked to this post which I'm not sure is exactly the same since their error message is on a different line (line 9 vs 14) and doesn't mention openssl like my error message does.
You may be to get a precompiled binary with OpenSSL 1.1 statically linked. Maybe Traveling Ruby? https://github.com/phusion/traveling-ruby
I would edit ossl.c and copy some code from Ruby OpenSSL commit 8e98d2e. This might be easier than building an old version of OpenSSL.