diff --git a/lib/rubygems/command_manager.rb b/lib/rubygems/command_manager.rb
index 03cdd6a4bb..e421f89884 100644
--- a/lib/rubygems/command_manager.rb
+++ b/lib/rubygems/command_manager.rb
@@ -148,7 +148,12 @@ class Gem::CommandManager
   def run(args, build_args=nil)
     process_args(args, build_args)
   rescue StandardError, Timeout::Error => ex
-    alert_error clean_text("While executing gem ... (#{ex.class})\n    #{ex}")
+    if ex.respond_to?(:detailed_message)
+      msg = ex.detailed_message(highlight: false).sub(/\A(.*?)(?: \(.+?\))/) { $1 }
+    else
+      msg = ex.message
+    end
+    alert_error clean_text("While executing gem ... (#{ex.class})\n    #{msg}")
     ui.backtrace ex
 
     terminate_interaction(1)
diff --git a/test/rubygems/test_gem_command_manager.rb b/test/rubygems/test_gem_command_manager.rb
index bee635d67e..00197d10f7 100644
--- a/test/rubygems/test_gem_command_manager.rb
+++ b/test/rubygems/test_gem_command_manager.rb
@@ -80,7 +80,13 @@ class TestGemCommandManager < Gem::TestCase
       message << "\nDid you mean?  \"push\""
     end
 
-    assert_equal message, e.message
+    if e.respond_to?(:detailed_message)
+      actual_message = e.detailed_message(highlight: false).sub(/\A(.*?)(?: \(.+?\))/) { $1 }
+    else
+      actual_message = e.message
+    end
+
+    assert_equal message, actual_message
   end
 
   def test_run_interrupt