Error "Failed to build gem native extension." when running "gem install openssl" in Fedora

[sergioro9]

Error "Failed to build gem native extension." when running "gem install openssl" in Fedora

[rhenium]

Installing openssl gem by default searches the same paths used when your Ruby was installed. Your Ruby 3.0.3 seems to be using the OpenSSL 1.0.1i (which is a very, very old release with known vulnerabilities - I'd upgrade it now), which is no longer supported by the latest openssl gem release, hence the first error.

Fedora's OpenSSL 3.0.9 is in /usr. Does gem install openssl -- --with-openssl-dir=/usr work?

[junaruga]

In your case, I assume that you installed Ruby 3.0.3 via RVM when the openssl-devel RPM veresion was 1.0.1i in the past, then you upgraded Fedora to new versions, and now the openssl-devel RPM version is 3.0.9. That means perhaps you don't need the --with-openssl-dir option now.

[sergioro9]

Solved the issue by installing Ruby 3.2.3 which supports OpenSSL 3, which is the OpenSSL version installed in my Fedora 38 server.

I used this command to install ruby:

rvm install 3.2.3

The problem was that Ruby versions below 3.1 do not support OpenSSL 3 according to rbenv/ruby-build#1940 (comment)

[sergioro9]

Found out a similar issue #686. It seems that the header files of my rvm ruby installation are OpenSSL 1.0.1 which is different from my system-wide OpenSSL version.

$ grep OPENSSL_VERSION /home/deploy/.rvm/usr/include/openssl/opensslv.h
#define OPENSSL_VERSION_NUMBER	0x1000109fL
#define OPENSSL_VERSION_TEXT	"OpenSSL 1.0.1i-fips 6 Aug 2014"
#define OPENSSL_VERSION_TEXT	"OpenSSL 1.0.1i 6 Aug 2014"
#define OPENSSL_VERSION_PTEXT	" part of " OPENSSL_VERSION_TEXT

$ grep OPENSSL_VERSION /usr/include/openssl/opensslv.h
# define OPENSSL_VERSION_MAJOR  3
# define OPENSSL_VERSION_MINOR  0
# define OPENSSL_VERSION_PATCH  9
...

It seems that I need to reinstall ruby with something like rvm reinstall 3.0.3 --with-openssl-dir=OpenSSL3-0-9-Directory. But I am not sure what the value for --with-openssl-dir should be.