https://git.ruby-lang.org/ruby.git/commit/?id=7529c53891

From 7529c538915cd1765b0a362ca64e8f8ff439d7fc Mon Sep 17 00:00:00 2001
From: Jeremy Evans <code@j...>
Date: Tue, 4 Jan 2022 10:22:37 -0800
Subject: [ruby/net-http] Do not set SNI hostname if connecting to IP address

RFC 6066, section 3, explicitly disallows the use of an IP address
as an SNI server name.  So check if the connection is being made
to an IP address using the resolv regexps, and do not set an SNI
hostname in that case.

Recent changes to LibreSSL make it more strictly follow RFC 6066,
resulting an s.hostname= raising an error if passed an IP address.
When such verions of LibreSSL are used, this change not only fixes
the net/http tests, it also fixes tests for webrick and open-uri,
which both make SSL connections to 127.0.0.1 using net/http in
their tests.

Avoid warning in the openssl extension by unsetting
@ssl_context.verify_hostname if connecting to an IP address.
Make changes so that the post_connection_check still happens
when connecting to an IP address, which is necessary to keep
checking that the certificate returned includes the IP address,
which one of the tests depends on.

Revert the previous change that modified the regexp used for
checking the error message.

https://github.com/ruby/net-http/commit/fa68e64bee
---
 lib/net/http.rb             | 24 +++++++++++++++++++++---
 test/net/http/test_https.rb |  2 +-
 2 files changed, 22 insertions(+), 4 deletions(-)

diff --git a/lib/net/http.rb b/lib/net/http.rb
index 1e7c91298e..3fcf23b05c 100644
--- a/lib/net/http.rb
+++ b/lib/net/http.rb
@@ -22,6 +22,7 @@ https://github.com/ruby/ruby/blob/trunk/lib/net/http.rb#L22
 
 require 'net/protocol'
 require 'uri'
+require 'resolv'
 autoload :OpenSSL, 'openssl'
 
 module Net   #:nodoc:
@@ -1036,17 +1037,34 @@ module Net   #:nodoc: https://github.com/ruby/ruby/blob/trunk/lib/net/http.rb#L1037
           OpenSSL::SSL::SSLContext::SESSION_CACHE_CLIENT |
           OpenSSL::SSL::SSLContext::SESSION_CACHE_NO_INTERNAL_STORE
         @ssl_context.session_new_cb = proc {|sock, sess| @ssl_session = sess }
+
+        # Still do the post_connection_check below even if connecting
+        # to IP address
+        verify_hostname = @ssl_context.verify_hostname
+
+        # Server Name Indication (SNI) RFC 3546/6066
+        case @address
+        when Resolv::IPv4::Regex, Resolv::IPv6::Regex
+          # don't set SNI, as IP addresses in SNI is not valid
+          # per RFC 6066, section 3.
+
+          # Avoid openssl warning
+          @ssl_context.verify_hostname = false
+        else
+          ssl_host_address = @address
+        end
+
         debug "starting SSL for #{conn_addr}:#{conn_port}..."
         s = OpenSSL::SSL::SSLSocket.new(s, @ssl_context)
         s.sync_close = true
-        # Server Name Indication (SNI) RFC 3546
-        s.hostname = @address if s.respond_to? :hostname=
+        s.hostname = ssl_host_address if s.respond_to?(:hostname=) && ssl_host_address
+
         if @ssl_session and
            Process.clock_gettime(Process::CLOCK_REALTIME) < @ssl_session.time.to_f + @ssl_session.timeout
           s.session = @ssl_session
         end
         ssl_socket_connect(s, @open_timeout)
-        if (@ssl_context.verify_mode != OpenSSL::SSL::VERIFY_NONE) && @ssl_context.verify_hostname
+        if (@ssl_context.verify_mode != OpenSSL::SSL::VERIFY_NONE) && verify_hostname
           s.post_connection_check(@address)
         end
         debug "SSL established, protocol: #{s.ssl_version}, cipher: #{s.cipher[0]}"
diff --git a/test/net/http/test_https.rb b/test/net/http/test_https.rb
index 603d6ecc1a..f4f1959a0e 100644
--- a/test/net/http/test_https.rb
+++ b/test/net/http/test_https.rb
@@ -255,7 +255,7 @@ class TestNetHTTPS < Test::Unit::TestCase https://github.com/ruby/ruby/blob/trunk/test/net/http/test_https.rb#L255
     ex = assert_raise(OpenSSL::SSL::SSLError){
       http.request_get("/") {|res| }
     }
-    re_msg = /certificate verify failed|hostname \"#{HOST_IP}\" does not match|ssl3 ext invalid servername/
+    re_msg = /certificate verify failed|hostname \"#{HOST_IP}\" does not match/
     assert_match(re_msg, ex.message)
   end
 
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