diff --git a/lib/msf/ui/console/command_dispatcher/developer.rb b/lib/msf/ui/console/command_dispatcher/developer.rb
index c18505e42f..b23bb7f4b1 100644
--- a/lib/msf/ui/console/command_dispatcher/developer.rb
+++ b/lib/msf/ui/console/command_dispatcher/developer.rb
@@ -5,8 +5,9 @@ class Msf::Ui::Console::CommandDispatcher::Developer
   include Msf::Ui::Console::CommandDispatcher
 
   @@irb_opts = Rex::Parser::Arguments.new(
-    "-h" => [ false, "Help banner."                                   ],
-    "-e" => [ true,  "Expression to evaluate."                        ])
+    '-h' => [false, 'Help menu.'             ],
+    '-e' => [true,  'Expression to evaluate.']
+  )
 
   def initialize(driver)
     super
@@ -18,11 +19,11 @@ class Msf::Ui::Console::CommandDispatcher::Developer
 
   def commands
     {
-      'irb'        => 'Drop into irb scripting mode',
-      'pry'        => 'Open a Pry session on the current module or Framework',
+      'irb'        => 'Open an interactive Ruby shell in the current context',
+      'pry'        => 'Open the Pry debugger on the current module or Framework',
       'edit'       => 'Edit the current module or a file with the preferred editor',
-      'reload_lib' => 'Reload one or more library files from specified paths',
-      'log'        => 'Displays framework.log starting at the bottom if possible'
+      'reload_lib' => 'Reload Ruby library files from specified paths',
+      'log'        => 'Display framework.log paged to the end if possible'
     }
   end
 
@@ -35,31 +36,52 @@ class Msf::Ui::Console::CommandDispatcher::Developer
   end
 
   # XXX: This will try to reload *any* .rb and break on modules
-  def reload_file(path)
-    unless File.exist?(path) && path.end_with?('.rb')
-      print_error("#{path} must exist and be a .rb file")
+  def reload_file(path, print_errors: true)
+    full_path = File.expand_path(path)
+
+    unless File.exist?(full_path) && full_path.end_with?('.rb')
+      print_error("#{full_path} must exist and be a .rb file") if print_errors
       return
     end
 
     # The file must exist to reach this, so we try our best here
-    if path =~ %r{^(?:\./)?modules/}
-      print_error("Reloading Metasploit modules is not supported (try 'reload')")
+    if full_path.start_with?(Msf::Config.module_directory, Msf::Config.user_module_directory)
+      print_error('Reloading Metasploit modules is not supported (try "reload")') if print_errors
       return
     end
 
-    print_status("Reloading #{path}")
-    load path
+    print_status("Reloading #{full_path}")
+    load full_path
+  end
+
+  def reload_changed_files
+    # Using an array avoids shelling out, so we avoid escaping/quoting
+    changed_files = %w[git diff --name-only]
+
+    output, status = Open3.capture2e(*changed_files, chdir: Msf::Config.install_root)
+
+    unless status.success?
+      print_error("Git is not available: #{output.chomp}")
+      return
+    end
+
+    files = output.split("\n")
+
+    files.each do |file|
+      f = File.join(Msf::Config.install_root, file)
+      reload_file(file, print_errors: false)
+    end
   end
 
   def cmd_irb_help
-    print_line "Usage: irb"
+    print_line 'Usage: irb'
     print_line
-    print_line "Execute commands in a Ruby environment"
+    print_line 'Open an interactive Ruby shell in the current context.'
     print @@irb_opts.usage
   end
 
   #
-  # Goes into IRB scripting mode
+  # Open an interactive Ruby shell in the current context
   #
   def cmd_irb(*args)
     expressions = []
@@ -76,10 +98,16 @@ class Msf::Ui::Console::CommandDispatcher::Developer
     end
 
     if expressions.empty?
-      print_status("Starting IRB shell...\n")
+      print_status('Starting IRB shell...')
 
       begin
-        Rex::Ui::Text::IrbShell.new(binding).run
+        if active_module
+          print_status("You are in #{active_module.fullname}\n")
+          Rex::Ui::Text::IrbShell.new(active_module).run
+        else
+          print_status("You are in the \"framework\" object\n")
+          Rex::Ui::Text::IrbShell.new(framework).run
+        end
       rescue
         print_error("Error during IRB: #{$!}\n\n#{$@.join("\n")}")
       end
@@ -89,6 +117,11 @@ class Msf::Ui::Console::CommandDispatcher::Developer
         driver.input.reset_tab_completion
       end
     else
+      # XXX: No vprint_status here either
+      if framework.datastore['VERBOSE'].to_s == 'true'
+        print_status("You are executing expressions in #{binding.receiver}")
+      end
+
       expressions.each { |expression| eval(expression, binding) }
     end
   end
@@ -104,12 +137,12 @@ class Msf::Ui::Console::CommandDispatcher::Developer
   def cmd_pry_help
     print_line 'Usage: pry'
     print_line
-    print_line 'Open a Pry session on the current module or Framework.'
+    print_line 'Open the Pry debugger on the current module or Framework.'
     print_line
   end
 
   #
-  # Open a Pry session on the current module or Framework
+  # Open the Pry debugger on the current module or Framework
   #
   def cmd_pry(*args)
     if args.include?('-h')
@@ -141,7 +174,7 @@ class Msf::Ui::Console::CommandDispatcher::Developer
     print_line
     print_line "Edit the currently active module or a local file with #{local_editor}."
     print_line 'If a library file is specified, it will automatically be reloaded after editing.'
-    print_line "Otherwise, you can reload the active module with 'reload' or 'rerun'."
+    print_line 'Otherwise, you can reload the active module with "reload" or "rerun".'
     print_line
   end
 
@@ -192,22 +225,32 @@ class Msf::Ui::Console::CommandDispatcher::Developer
   end
 
   def cmd_reload_lib_help
-    print_line 'Usage: reload_lib lib/to/reload.rb [...]'
-    print_line
-    print_line 'Reload one or more library files from specified paths.'
-    print_line
+    cmd_reload_lib('-h')
   end
 
   #
-  # Reload one or more library files from specified paths
+  # Reload Ruby library files from specified paths
   #
   def cmd_reload_lib(*args)
-    if args.empty? || args.include?('-h') || args.include?('--help')
-      cmd_reload_lib_help
-      return
+    options = OptionParser.new do |opts|
+      opts.banner = 'Usage: reload_lib lib/to/reload.rb [...]'
+      opts.separator ''
+      opts.separator 'Reload Ruby library files from specified paths.'
+      opts.separator ''
+
+      opts.on '-h', '--help', 'Help banner.' do
+        return print(opts.help)
+      end
+
+      opts.on '-a', '--all', 'Reload all* changed files in your current Git working tree.
+                                     *Excludes modules and non-Ruby files.' do
+        reload_changed_files
+        return
+      end
     end
 
-    args.each { |path| reload_file(path) }
+    files = options.order(args)
+    files.each { |file| reload_file(file) }
   end
 
   #
@@ -220,15 +263,15 @@ class Msf::Ui::Console::CommandDispatcher::Developer
   def cmd_log_help
     print_line 'Usage: log'
     print_line
-    print_line 'Displays framework.log starting at the bottom if possible.'
-    print_line "For full effect, 'setg LogLevel 3' before running modules."
+    print_line 'Display framework.log paged to the end if possible.'
+    print_line 'For full effect, "setg LogLevel 3" before running modules.'
     print_line
     print_line "Log location: #{File.join(Msf::Config.log_directory, 'framework.log')}"
     print_line
   end
 
   #
-  # Displays framework.log starting at the bottom if possible
+  # Display framework.log paged to the end if possible
   #
   def cmd_log(*args)
     path = File.join(Msf::Config.log_directory, 'framework.log')
diff --git a/lib/rex/post/meterpreter/ui/console/command_dispatcher/core.rb b/lib/rex/post/meterpreter/ui/console/command_dispatcher/core.rb
index 352f6b6865..83428ec73a 100644
--- a/lib/rex/post/meterpreter/ui/console/command_dispatcher/core.rb
+++ b/lib/rex/post/meterpreter/ui/console/command_dispatcher/core.rb
@@ -34,12 +34,14 @@ class Console::CommandDispatcher::Core
   end
 
   @@irb_opts = Rex::Parser::Arguments.new(
-    '-h' => [false, 'Help banner.'],
-    '-e' => [true,  'Expression to evaluate.'])
+    '-h' => [false, 'Help menu.'             ],
+    '-e' => [true,  'Expression to evaluate.']
+  )
 
   @@load_opts = Rex::Parser::Arguments.new(
-    '-l' => [false, 'List all available extensions'],
-    '-h' => [false, 'Help menu.'])
+    '-h' => [false, 'Help menu.'                    ],
+    '-l' => [false, 'List all available extensions.']
+  )
 
   #
   # List of supported commands.
@@ -52,8 +54,8 @@ class Console::CommandDispatcher::Core
       'channel'      => 'Displays information or control active channels',
       'exit'         => 'Terminate the meterpreter session',
       'help'         => 'Help menu',
-      'irb'          => 'Drop into irb scripting mode',
-      'pry'          => 'Open a Pry session on the current session',
+      'irb'          => 'Open an interactive Ruby shell on the current session',
+      'pry'          => 'Open the Pry debugger on the current session',
       'use'          => 'Deprecated alias for "load"',
       'load'         => 'Load one or more meterpreter extensions',
       'machine_id'   => 'Get the MSF ID of the machine attached to the session',
@@ -532,7 +534,7 @@ class Console::CommandDispatcher::Core
   def cmd_irb_help
     print_line('Usage: irb')
     print_line
-    print_line('Execute commands in a Ruby environment')
+    print_line('Open an interactive Ruby shell on the current session.')
     print @@irb_opts.usage
   end
 
@@ -542,7 +544,7 @@ class Console::CommandDispatcher::Core
   end
 
   #
-  # Runs the IRB scripting shell
+  # Open an interactive Ruby shell on the current session
   #
   def cmd_irb(*args)
     expressions = []
@@ -561,12 +563,16 @@ class Console::CommandDispatcher::Core
     framework = client.framework
 
     if expressions.empty?
-      print_status('Starting IRB shell')
-      print_status('The "client" variable holds the meterpreter client')
-      print_line
+      print_status('Starting IRB shell...')
+      print_status("You are in the \"client\" (session) object\n")
 
-      Rex::Ui::Text::IrbShell.new(binding).run
+      Rex::Ui::Text::IrbShell.new(client).run
     else
+      # XXX: No vprint_status here
+      if framework.datastore['VERBOSE'].to_s == 'true'
+        print_status("You are executing expressions in #{binding.receiver}")
+      end
+
       expressions.each { |expression| eval(expression, binding) }
     end
   end
@@ -574,12 +580,12 @@ class Console::CommandDispatcher::Core
   def cmd_pry_help
     print_line 'Usage: pry'
     print_line
-    print_line 'Open a Pry session on the current session.'
+    print_line 'Open the Pry debugger on the current session.'
     print_line
   end
 
   #
-  # Open a Pry session on the current session
+  # Open the Pry debugger on the current session
   #
   def cmd_pry(*args)
     if args.include?('-h')