Created attachment 518054 [details] build.log While building dev-lang/ruby-2.3.6 (with 'ssl' USE flag enabled), I noticed the following in the build output: ../.././ext/openssl/extconf.rb Ignore OpenSSL broken by Apple. Please use another openssl. (e.g. using `configure --with-openssl-dir=/path/to/openssl') Failed to configure openssl. It will not be installed. However the build proceeded fine. I checked, and indeed Ruby 2.3 does not seem to properly detect OpenSSL 1.1.0, so it silently disables the OpenSSL module. This is likely to cause errors down the road. The failed detection is due to OpenSSL 1.1.0 deprecating and removing declarations from its headers. I'm attaching a patch that fixes detection (for the 2.3 branch). The patch has also been submitted upstream: https://github.com/ruby/ruby/pull/1810
Created attachment 518056 [details, diff] ruby-2.3.6-openssl1.1-detection.patch
Comment on attachment 518056 [details, diff] ruby-2.3.6-openssl1.1-detection.patch I'm retracting from my previous statement: this patch does fix OpenSSL 1.1.0 detection, but the build still fails, silently. So this is still an issue, but I don't have a fix. Backporting OpenSSL 1.1.0 compatibility from Ruby 2.5 is too much work for me right now.
I think it's pretty clear that we're not going to be creating a patch for Ruby 2.3 to support OpenSSL 1.1 any time soon, and upstream isn't going to do it for us. So I think the solution is to update the ruby 2.3 ebuilds to request <dev-lib/openssl-1.1 and call it day; I've submitted a pull request to do that: https://github.com/gentoo/gentoo/pull/10606
The bug has been closed via the following commit(s): https://gitweb.gentoo.org/repo/gentoo.git/commit/?id=51ae16ec01c1575c8335066aa2620d8bc3bede0e commit 51ae16ec01c1575c8335066aa2620d8bc3bede0e Author: Hans de Graaff <graaff@gentoo.org> AuthorDate: 2018-12-11 09:08:25 +0000 Commit: Hans de Graaff <graaff@gentoo.org> CommitDate: 2018-12-11 09:48:06 +0000 dev-lang/ruby: 2.3 requires <dev-libs/openssl-1.1 Ruby 2.3 does not compile with dev-libs/openssl-1.1.0 or newer and this will not be fixed upstream since ruby 2.3 is EOL in March 2019 and currently only receives security fixes. Thanks to candrews for the proposed approach to this. Fixes: https://bugs.gentoo.org/646734 Package-Manager: Portage-2.3.51, Repoman-2.3.11 Signed-off-by: Hans de Graaff <graaff@gentoo.org> dev-lang/ruby/Manifest | 1 + dev-lang/ruby/ruby-2.3.8-r1.ebuild | 242 +++++++++++++++++++++++++++++++++++++ 2 files changed, 243 insertions(+)