diff --git a/lib/msf/ui/console/command_dispatcher/developer.rb b/lib/msf/ui/console/command_dispatcher/developer.rb
index ee3c1ba4c3530..c18505e42fdf1 100644
--- a/lib/msf/ui/console/command_dispatcher/developer.rb
+++ b/lib/msf/ui/console/command_dispatcher/developer.rb
@@ -112,14 +112,28 @@ def cmd_pry_help
   # Open a Pry session on the current module or Framework
   #
   def cmd_pry(*args)
+    if args.include?('-h')
+      cmd_pry_help
+      return
+    end
+
     begin
       require 'pry'
     rescue LoadError
-      print_error("Failed to load Pry, try 'gem install pry'")
+      print_error('Failed to load Pry, try "gem install pry"')
+      return
+    end
+
+    print_status('Starting Pry shell...')
+
+    unless active_module
+      print_status("You are in the \"framework\" object\n")
+      framework.pry
       return
     end
 
-    active_module ? active_module.pry : framework.pry
+    print_status("You are in #{active_module.fullname}\n")
+    active_module.pry
   end
 
   def cmd_edit_help
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 bc52066bb7453..352f6b6865fbf 100644
--- a/lib/rex/post/meterpreter/ui/console/command_dispatcher/core.rb
+++ b/lib/rex/post/meterpreter/ui/console/command_dispatcher/core.rb
@@ -53,7 +53,7 @@ def commands
       'exit'         => 'Terminate the meterpreter session',
       'help'         => 'Help menu',
       'irb'          => 'Drop into irb scripting mode',
-      'pry'          => 'Open a Pry session on the client object',
+      'pry'          => 'Open a Pry session 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',
@@ -574,21 +574,29 @@ def cmd_irb(*args)
   def cmd_pry_help
     print_line 'Usage: pry'
     print_line
-    print_line 'Open a Pry session on the client object.'
+    print_line 'Open a Pry session on the current session.'
     print_line
   end
 
   #
-  # Open a Pry session on the client object
+  # Open a Pry session on the current session
   #
   def cmd_pry(*args)
+    if args.include?('-h')
+      cmd_pry_help
+      return
+    end
+
     begin
       require 'pry'
     rescue LoadError
-      print_error("Failed to load Pry, try 'gem install pry'")
+      print_error('Failed to load Pry, try "gem install pry"')
       return
     end
 
+    print_status('Starting Pry shell...')
+    print_status("You are in the \"client\" (session) object\n")
+
     client.pry
   end