Hi, context is 12.0-BETA3 r340208 GENERIC amd64 ports is Revision: 484403 nothing pertaining to openssl in make.conf or src.conf I ran make check-old and yes | make delete-old and yes | make delete-old-libs then rebooted before attempting to upgrade ruby # openssl version OpenSSL 1.1.1-freebsd 11 Sep 2018 /usr/ports/lang/ruby23 # make [...] generating amd64-freebsd12-fake.rb amd64-freebsd12-fake.rb updated ./miniruby -I./lib -I. -I.ext/common ./tool/runruby.rb --extout=.ext -- --disable-gems -r./amd64-freebsd12-fake ./tool/rbinstall.rb --make="/usr/bin/make" --dest-dir="/usr/ports/lang/ruby23/work/stage" --extout=".ext" --mflags=" " --make-flags=" .MAKE.LEVEL.ENV=MAKELEVEL ARCH=amd64 CONFIGURE_MAX_CMD_LEN=262144 CONFIG_DONE_RUBY23=1 DESTDIR=/usr/ports/lang/ruby23/work/stage HAVE_COMPAT_IA32_KERN=YES\ OPSYS=FreeBSD OSREL=12.0 OSVERSION=1200086 _OSRELEASE=12.0-BETA3 _PERL5_FROM_BIN=5.26.2 _PKG_CHECKED=1" --data-mode=0644 --prog-mode=0755 --installed-list .installed.list --mantype="man" --install=all --rdoc-output=".ext/rdoc" /usr/ports/lang/ruby23/work/ruby-2.3.8/lib/rubygems/core_ext/kernel_require.rb:55:in `require': Shared object "libssl.so.8" not found, required by "openssl.so" - /usr/local/lib/ruby/2.3/amd64-freebsd12/openssl.so (LoadError) from /usr/ports/lang/ruby23/work/ruby-2.3.8/lib/rubygems/core_ext/kernel_require.rb:55:in `require' from /usr/local/lib/ruby/2.3/openssl.rb:13:in `<top (required)>' from /usr/ports/lang/ruby23/work/ruby-2.3.8/lib/rubygems/core_ext/kernel_require.rb:55:in `require' from /usr/ports/lang/ruby23/work/ruby-2.3.8/lib/rubygems/core_ext/kernel_require.rb:55:in `require' from /usr/ports/lang/ruby23/work/ruby-2.3.8/lib/rubygems/security.rb:12:in `<top (required)>' from /usr/ports/lang/ruby23/work/ruby-2.3.8/lib/rubygems/core_ext/kernel_require.rb:55:in `require' from /usr/ports/lang/ruby23/work/ruby-2.3.8/lib/rubygems/core_ext/kernel_require.rb:55:in `require' from /usr/ports/lang/ruby23/work/ruby-2.3.8/lib/rubygems/package.rb:44:in `<top (required)>' from /usr/ports/lang/ruby23/work/ruby-2.3.8/lib/rubygems/core_ext/kernel_require.rb:55:in `require' from /usr/ports/lang/ruby23/work/ruby-2.3.8/lib/rubygems/core_ext/kernel_require.rb:55:in `require' from /usr/ports/lang/ruby23/work/ruby-2.3.8/lib/rubygems/installer.rb:10:in `<top (required)>' from /usr/ports/lang/ruby23/work/ruby-2.3.8/lib/rubygems/core_ext/kernel_require.rb:55:in `require' from /usr/ports/lang/ruby23/work/ruby-2.3.8/lib/rubygems/core_ext/kernel_require.rb:55:in `require' from ./tool/rbinstall.rb:658:in `<module:RbInstall>' from ./tool/rbinstall.rb:586:in `<main>' *** Error code 1 Stop. make[2]: stopped in /usr/ports/lang/ruby23/work/ruby-2.3.8 *** Error code 1 Stop. make[1]: stopped in /usr/ports/lang/ruby23 *** Error code 1 Stop. make: stopped in /usr/ports/lang/ruby23 how can I fix please? thanks, -- J.