diff --git a/Rakefile b/Rakefile
index 1b97d30546b..e313627e319 100755
--- a/Rakefile
+++ b/Rakefile
@@ -34,11 +34,11 @@ Rake::ExtensionTask.new('grpc_c', spec) do |ext|
     'universal-darwin'
   ]
   ext.cross_compiling do |spec|
-    spec.files = %w( etc/roots.pem grpc_c.32.ruby grpc_c.64.ruby )
-    spec.files += Dir.glob('src/ruby/bin/**/*')
-    spec.files += Dir.glob('src/ruby/ext/**/*')
-    spec.files += Dir.glob('src/ruby/lib/**/*')
-    spec.files += Dir.glob('src/ruby/pb/**/*')
+    spec.files = spec.files.select {
+      |file| file.start_with?(
+        "src/ruby/bin/", "src/ruby/ext/", "src/ruby/lib/", "src/ruby/pb/")
+    }
+    spec.files += %w( etc/roots.pem grpc_c.32.ruby grpc_c.64.ruby )
   end
 end
 
diff --git a/grpc.gemspec b/grpc.gemspec
index 99a3fcd8c77..652b1f75440 100644
--- a/grpc.gemspec
+++ b/grpc.gemspec
@@ -19,15 +19,13 @@ Gem::Specification.new do |s|
   s.files += %w( etc/roots.pem )
   s.files += Dir.glob('src/ruby/bin/**/*')
   s.files += Dir.glob('src/ruby/ext/**/*')
-  s.files += Dir.glob('src/ruby/lib/**/*').reject do |f|
-    # Binaries are included by rake-compiler and would lead to circular dependencies here
-    File.fnmatch("**/?.?/grpc_c.so", f)
-  end
+  s.files += Dir.glob('src/ruby/lib/**/*')
   s.files += Dir.glob('src/ruby/pb/**/*').reject do |f|
     f.match(%r{^src/ruby/pb/test})
   end
   s.files += Dir.glob('include/grpc/**/*')
   s.test_files = Dir.glob('src/ruby/spec/**/*')
+  s.test_files += Dir.glob('src/ruby/pb/test/**/*')
   s.bindir = 'src/ruby/bin'
   s.require_paths = %w( src/ruby/lib src/ruby/bin src/ruby/pb )
   s.platform      = Gem::Platform::RUBY
diff --git a/src/ruby/lib/grpc/grpc.rb b/src/ruby/lib/grpc/grpc.rb
index f52efe36764..89944aea7fa 100644
--- a/src/ruby/lib/grpc/grpc.rb
+++ b/src/ruby/lib/grpc/grpc.rb
@@ -16,7 +16,7 @@ begin
   ruby_version_dirname = /(\d+\.\d+)/.match(RUBY_VERSION).to_s
   distrib_lib_dir = File.expand_path(ruby_version_dirname,
                                      File.dirname(__FILE__))
-  if File.directory?(distrib_lib_dir)
+  if !Dir.glob("#{distrib_lib_dir}/grpc_c*").empty?
     require "#{distrib_lib_dir}/grpc_c"
   else
     require 'grpc/grpc_c'
diff --git a/templates/grpc.gemspec.template b/templates/grpc.gemspec.template
index faf88f170ab..b43727c71c7 100644
--- a/templates/grpc.gemspec.template
+++ b/templates/grpc.gemspec.template
@@ -21,15 +21,13 @@
     s.files += %w( etc/roots.pem )
     s.files += Dir.glob('src/ruby/bin/**/*')
     s.files += Dir.glob('src/ruby/ext/**/*')
-    s.files += Dir.glob('src/ruby/lib/**/*').reject do |f|
-      # Binaries are included by rake-compiler and would lead to circular dependencies here
-      File.fnmatch("**/?.?/grpc_c.so", f)
-    end
+    s.files += Dir.glob('src/ruby/lib/**/*')
     s.files += Dir.glob('src/ruby/pb/**/*').reject do |f|
       f.match(%r{^src/ruby/pb/test})
     end
     s.files += Dir.glob('include/grpc/**/*')
     s.test_files = Dir.glob('src/ruby/spec/**/*')
+    s.test_files += Dir.glob('src/ruby/pb/test/**/*')
     s.bindir = 'src/ruby/bin'
     s.require_paths = %w( src/ruby/lib src/ruby/bin src/ruby/pb )
     s.platform      = Gem::Platform::RUBY