diff --git a/lib/rubygems/package.rb b/lib/rubygems/package.rb
index 084dc5d2d9..4672866985 100644
--- a/lib/rubygems/package.rb
+++ b/lib/rubygems/package.rb
@@ -444,10 +444,10 @@ EOM
           directories << mkdir
         end
 
-        File.open destination, "wb" do |out|
-          out.write entry.read
+        if entry.file?
+          File.open(destination, "wb") {|out| out.write entry.read }
           FileUtils.chmod file_mode(entry.header.mode), destination
-        end if entry.file?
+        end
 
         verbose destination
       end
@@ -467,7 +467,12 @@ EOM
   end
 
   def file_mode(mode) # :nodoc:
-    ((mode & 0111).zero? ? data_mode : prog_mode) || mode
+    ((mode & 0111).zero? ? data_mode : prog_mode) ||
+      # If we're not using one of the default modes, then we're going to fall
+      # back to the mode from the tarball. In this case we need to mask it down
+      # to fit into 2^16 bits (the maximum value for a mode in CRuby since it
+      # gets put into an unsigned short).
+      (mode & ((1 << 16) - 1))
   end
 
   ##
diff --git a/test/rubygems/packages/Bluebie-legs-0.6.2.gem b/test/rubygems/packages/Bluebie-legs-0.6.2.gem
new file mode 100644
index 0000000000..60918f3bc5
Binary files /dev/null and b/test/rubygems/packages/Bluebie-legs-0.6.2.gem differ
diff --git a/test/rubygems/test_gem_package.rb b/test/rubygems/test_gem_package.rb
index 9295f42dba..eebe4d86d0 100644
--- a/test/rubygems/test_gem_package.rb
+++ b/test/rubygems/test_gem_package.rb
@@ -510,6 +510,21 @@ class TestGemPackage < Gem::Package::TarTestCase
     assert_path_exist @destination
   end
 
+  def test_extract_file_permissions
+    pend "chmod not supported" if win_platform?
+
+    gem_with_long_permissions = File.expand_path("packages/Bluebie-legs-0.6.2.gem", __dir__)
+
+    package = Gem::Package.new gem_with_long_permissions
+
+    package.extract_files @destination
+
+    filepath = File.join @destination, "README.rdoc"
+    assert_path_exist filepath
+
+    assert_equal 0104444, File.stat(filepath).mode
+  end
+
   def test_extract_tar_gz_absolute
     package = Gem::Package.new @gem