1 files changed, 4 insertions, 3 deletions
diff --git a/lib/rubygems/request.rb b/lib/rubygems/request.rb
index 75f9e9979a..1ed0fbcb99 100644
--- a/lib/rubygems/request.rb
+++ b/lib/rubygems/request.rb
@@ -1,6 +1,5 @@
 # frozen_string_literal: true
 require 'net/http'
-require 'time'
 require 'rubygems/user_interaction'
 
 class Gem::Request
@@ -45,7 +44,8 @@ class Gem::Request
   end
 
   def self.configure_connection_for_https(connection, cert_files)
-    require 'openssl'
+    raise Gem::Exception.new('OpenSSl is not available. Install OpenSSL and rebuild Ruby (preferred) or use non-HTTPS sources') unless Gem::HAVE_OPENSSL
+
     connection.use_ssl = true
     connection.verify_mode =
       Gem.configuration.ssl_verify_mode || OpenSSL::SSL::VERIFY_PEER
@@ -125,7 +125,7 @@ class Gem::Request
 
   def connection_for(uri)
     @connection_pool.checkout
-  rescue defined?(OpenSSL::SSL) ? OpenSSL::SSL::SSLError : Errno::EHOSTDOWN,
+  rescue Gem::HAVE_OPENSSL ? OpenSSL::SSL::SSLError : Errno::EHOSTDOWN,
          Errno::EHOSTDOWN => e
     raise Gem::RemoteFetcher::FetchError.new(e.message, uri)
   end
@@ -143,6 +143,7 @@ class Gem::Request
     request.add_field 'Keep-Alive', '30'
 
     if @last_modified
+      require 'time'
       request.add_field 'If-Modified-Since', @last_modified.httpdate
     end