Group commands in "help" output

lib/pry/command.rb

@@ -129,6 +129,25 @@ class Pry
           obj
         end
       end
+
+      # The group in which the command should be displayed in "help" output.
+      # This is usually auto-generated from directory naming, but it can be
+      # manually overridden if necessary.
+      def group(name=nil)
+        @group = name if name
+        @group ||=(
+          case Pry::Method(block).source_file
+          when %r{/pry/.*_commands/(.*).rb}
+            $1.capitalize
+          when %r{/(pry-[^\/]*)/}
+            $1
+          when /pryrc/
+            "~/.pryrc"
+          else
+            "(other)"
+          end
+        )
+      end
     end
 
 

lib/pry/command_set.rb

@@ -350,16 +350,27 @@ class Pry
               output.puts "No info for command: #{cmd}"
             end
           else
-            output.puts
-            help_text = heading("Command List: ") + "\n"
+            grouped = commands.values.group_by(&:group)
 
-            help_text << commands.map do |key, command|
-              if command.description && !command.description.empty?
-                "#{command.options[:listing].to_s.ljust(18)} #{command.description}"
+            help_text = []
+
+            grouped.keys.sort.each do |key|
+
+              commands = grouped[key].select do |command|
+                command.description && !command.description.empty?
+              end.sort_by do |command|
+                command.options[:listing].to_s
               end
-            end.compact.sort.join("\n")
 
-            stagger_output(help_text)
+              unless commands.empty?
+                help_text << "  #{text.bold(key)}"
+                help_text += commands.map do |command|
+                  "#{command.options[:listing].to_s.ljust(18)} #{command.description}"
+                end
+              end
+            end
+
+            stagger_output(help_text.join("\n"))
           end
         end
       end