diff --git a/lib/rubygems.rb b/lib/rubygems.rb
index e750277dd3..9b563f21ee 100644
--- a/lib/rubygems.rb
+++ b/lib/rubygems.rb
@@ -1333,7 +1333,12 @@ begin
 rescue LoadError
   # Ignored
 rescue Exception => e
-  raise e.class, "#{e.message}\nThis is not expected so please report this issue to your OS support and ask for help."
+  msg = "#{e.message}\n" \
+    "Loading the rubygems/defaults/operating_system.rb file caused an error. " \
+    "This file is owned by your OS, not by rubygems upstream. " \
+    "Please find out which OS package this file belongs to and follow the guidelines from your OS to report " \
+    "the problem and ask for help."
+  raise e.class, msg
 end
 
 begin
diff --git a/test/rubygems/test_rubygems.rb b/test/rubygems/test_rubygems.rb
index 9aa6c20cf5..f94481dc24 100644
--- a/test/rubygems/test_rubygems.rb
+++ b/test/rubygems/test_rubygems.rb
@@ -15,7 +15,11 @@ class GemTest < Gem::TestCase
 
     output = Gem::Util.popen(*ruby_with_rubygems_and_fake_operating_system_in_load_path(path), '-e', "'require \"rubygems\"'", {:err => [:child, :out]}).strip
     assert !$?.success?
-    assert_includes output, "This is not expected so please report this issue to your OS support and ask for help"
+    assert_includes output, "unterminated string meets end of file (SyntaxError)"
+    assert_includes output, "Loading the rubygems/defaults/operating_system.rb file caused an error. " \
+    "This file is owned by your OS, not by rubygems upstream. " \
+    "Please find out which OS package this file belongs to and follow the guidelines from your OS to report " \
+    "the problem and ask for help."
   end
 
   private