Issue #8557 has been updated by drbrain (Eric Hodel).


I have this fixed on RubyGems master and will merge to ruby trunk after releasing RubyGems 2.0.4 (later this week).
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Bug #8557: rubygems/security.rb is loaded twice if openssl is unavailable
https://bugs.ruby-lang.org/issues/8557#change-40259

Author: nobu (Nobuyoshi Nakada)
Status: Assigned
Priority: Normal
Assignee: drbrain (Eric Hodel)
Category: lib/rubygems
Target version: current: 2.1.0
ruby -v: 2.1.0dev
Backport: 2.0.0: REQUIRED


=begin
Since r39606, ((%rubygems/security.rb%)) is loaded twice if ((%openssl%)) is unavailable.

  $ make TESTS=rubygems test-all
          CC = clang
          LD = ld
          LDSHARED = clang -dynamiclib
          CFLAGS = -O3 -fno-fast-math -ggdb3 -Wall -Wextra -Wno-unused-parameter -Wno-parentheses -Wno-long-long -Wno-missing-field-initializers -Wunused-variable -Werror=pointer-arith -Werror=write-strings -Werror=declaration-after-stateme
          XCFLAGS = -D_FORTIFY_SOURCE=2 -fstack-protector -fno-strict-overflow -fvisibility=hidden -DRUBY_EXPORT
          CPPFLAGS = -D_XOPEN_SOURCE -D_DARWIN_C_SOURCE -D_DARWIN_UNLIMITED_SELECT -D_REENTRANT   -I. -I.ext/include/x86_64-darwin11 -I../src/include -I../src
          DLDFLAGS = -Wl,-undefined,dynamic_lookup -Wl,-multiply_defined,suppress -install_name @executable_path/../lib/libruby.2.1.0.dylib -current_version 2.1.0 -compatibility_version 2.1.0  -fstack-protector -Wl,-u,_objc_msgSend  -fstack
          SOLIBS =
  Apple LLVM version 4.2 (clang-425.0.27) (based on LLVM 3.2svn)
  Target: x86_64-apple-darwin11.4.2
  Thread model: posix
  ./miniruby -I../src/lib -I. -I.ext/common  ../src/tool/runruby.rb --extout=.ext  -- --disable-gems "../src/test/runner.rb" --ruby="./miniruby -I../src/lib -I. -I.ext/common  ../src/tool/runruby.rb --extout=.ext  -- --disable-gems"  rubyge
  /Users/nobu/src/ruby/trunk/src/lib/rubygems/security.rb:355: warning: already initialized constant Gem::Security::DIGEST_ALGORITHM
  /Users/nobu/src/ruby/trunk/src/lib/rubygems/security.rb:355: warning: previous definition of DIGEST_ALGORITHM was here

 $ nmake TESTS=rubygems test-all
 	CC = cl -nologo
 	LD = cl -nologo
 	LDSHARED = cl -nologo -LD
 	CFLAGS = -MD -Zi -W2 -wd4996 -we4028 -we4142 -O2sy-  -Zm600
 	XCFLAGS = -DRUBY_EXPORT -I. -I.ext/include/i386-mswin32_110 -I../src/include -I../src -I../src/missing
 	CPPFLAGS =
 	DLDFLAGS = -incremental:no -debug -opt:ref -opt:icf -dll
 	SOLIBS =
 	.\ruby.exe -I../src/lib -I".ext/i386-mswin32_110" -I. "../src/tool/runruby.rb" --extout=".ext"	-- --disable-gems "../src/test/runner.rb" --ruby=".\ruby.exe -I../src/lib -I".ext/i386-mswin32_110" -I. "../src/tool/runruby.rb" --extout=".ext"  -- --disable-gems"  rubygems
 C:/Users/nobu/build/ruby/trunk/src/lib/rubygems/security.rb:355: warning: already initialized constant Gem::Security::DIGEST_ALGORITHM
 C:/Users/nobu/build/ruby/trunk/src/lib/rubygems/security.rb:355: warning: previous definition of DIGEST_ALGORITHM was here

It seems to intend to fake (({OpenSSL})) but doesn't work actually, because (({Gem::Security::Policy})) requires ((%openssl%)).

  $ ./bin/ruby -rrubygems/security -ep
  C:/Users/nobu/build/ruby/trunk/i386-mswin32_110/lib/ruby/vendor_ruby/rubygems/core_ext/kernel_require.rb:45:in `require': cannot load such file -- openssl (LoadError)
  	from C:/Users/nobu/build/ruby/trunk/i386-mswin32_110/lib/ruby/vendor_ruby/rubygems/core_ext/kernel_require.rb:45:in `require'
  	from C:/Users/nobu/build/ruby/trunk/i386-mswin32_110/lib/ruby/vendor_ruby/rubygems/security/policy.rb:23:in `initialize'
  	from C:/Users/nobu/build/ruby/trunk/i386-mswin32_110/lib/ruby/vendor_ruby/rubygems/security/policies.rb:6:in `new'
  	from C:/Users/nobu/build/ruby/trunk/i386-mswin32_110/lib/ruby/vendor_ruby/rubygems/security/policies.rb:6:in `<module:Security>'
  	from C:/Users/nobu/build/ruby/trunk/i386-mswin32_110/lib/ruby/vendor_ruby/rubygems/security/policies.rb:1:in `<top (required)>'
  	from C:/Users/nobu/build/ruby/trunk/i386-mswin32_110/lib/ruby/vendor_ruby/rubygems/core_ext/kernel_require.rb:45:in `require'
  	from C:/Users/nobu/build/ruby/trunk/i386-mswin32_110/lib/ruby/vendor_ruby/rubygems/core_ext/kernel_require.rb:45:in `require'
  	from C:/Users/nobu/build/ruby/trunk/i386-mswin32_110/lib/ruby/vendor_ruby/rubygems/security.rb:583:in `<top (required)>'
  	from C:/Users/nobu/build/ruby/trunk/i386-mswin32_110/lib/ruby/vendor_ruby/rubygems/core_ext/kernel_require.rb:45:in `require'
  	from C:/Users/nobu/build/ruby/trunk/i386-mswin32_110/lib/ruby/vendor_ruby/rubygems/core_ext/kernel_require.rb:45:in `require'
  bash: exit 1

 $ ./bin/ruby -rrubygems/security -ep
 /Users/nobu/build/ruby/trunk/x86_64-darwin/lib/ruby/vendor_ruby/rubygems/core_ext/kernel_require.rb:45:in `require': cannot load such file -- openssl (LoadError)
 	from /Users/nobu/build/ruby/trunk/x86_64-darwin/lib/ruby/vendor_ruby/rubygems/core_ext/kernel_require.rb:45:in `require'
 	from /Users/nobu/build/ruby/trunk/x86_64-darwin/lib/ruby/vendor_ruby/rubygems/security/policy.rb:23:in `initialize'
 	from /Users/nobu/build/ruby/trunk/x86_64-darwin/lib/ruby/vendor_ruby/rubygems/security/policies.rb:6:in `new'
 	from /Users/nobu/build/ruby/trunk/x86_64-darwin/lib/ruby/vendor_ruby/rubygems/security/policies.rb:6:in `<module:Security>'
 	from /Users/nobu/build/ruby/trunk/x86_64-darwin/lib/ruby/vendor_ruby/rubygems/security/policies.rb:1:in `<top (required)>'
 	from /Users/nobu/build/ruby/trunk/x86_64-darwin/lib/ruby/vendor_ruby/rubygems/core_ext/kernel_require.rb:45:in `require'
 	from /Users/nobu/build/ruby/trunk/x86_64-darwin/lib/ruby/vendor_ruby/rubygems/core_ext/kernel_require.rb:45:in `require'
 	from /Users/nobu/build/ruby/trunk/x86_64-darwin/lib/ruby/vendor_ruby/rubygems/security.rb:583:in `<top (required)>'
 	from /Users/nobu/build/ruby/trunk/x86_64-darwin/lib/ruby/vendor_ruby/rubygems/core_ext/kernel_require.rb:45:in `require'
 	from /Users/nobu/build/ruby/trunk/x86_64-darwin/lib/ruby/vendor_ruby/rubygems/core_ext/kernel_require.rb:45:in `require'
 bash: exit 1

Moreover, since (({LoadError#path})) returns required library name with its suffix, so (({e.path == 'openssl'})) never become true.
=end



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