1 files changed, 15 insertions, 8 deletions
diff --git a/lib/rubygems/commands/contents_command.rb b/lib/rubygems/commands/contents_command.rb
index 807158d9c9..bd0cbce8ba 100644
--- a/lib/rubygems/commands/contents_command.rb
+++ b/lib/rubygems/commands/contents_command.rb
@@ -103,16 +103,23 @@ prefix or only the files that are requireable.
 
   def files_in_default_gem(spec)
     spec.files.map do |file|
-      case file
-      when %r{\A#{spec.bindir}/}
-        # $' is POSTMATCH
-        [RbConfig::CONFIG["bindir"], $']
-      when /\.so\z/
-        [RbConfig::CONFIG["archdir"], file]
+      if file.start_with?("#{spec.bindir}/")
+        [RbConfig::CONFIG["bindir"], file.delete_prefix("#{spec.bindir}/")]
       else
-        [RbConfig::CONFIG["rubylibdir"], file]
+        gem spec.name, spec.version
+
+        require_path = spec.require_paths.find do |path|
+          file.start_with?("#{path}/")
+        end
+
+        requirable_part = file.delete_prefix("#{require_path}/")
+
+        resolve = $LOAD_PATH.resolve_feature_path(requirable_part)&.last
+        next unless resolve
+
+        [resolve.delete_suffix(requirable_part), requirable_part]
       end
-    end
+    end.compact
   end
 
   def gem_contents(name)