diff --git a/lib/pry/cli.rb b/lib/pry/cli.rb
index 66ae3e3e..781c2dbe 100644
--- a/lib/pry/cli.rb
+++ b/lib/pry/cli.rb
@@ -143,6 +143,10 @@ Copyright (c) 2013 John Mair (banisterfiend)
     Pry.plugins[plugin_name].disable!
   end
 
+  on :i, "interactive", "Go interactive after execution" do
+    Pry.config.exit_interactive = true
+  end
+
   on "no-plugins", "Suppress loading of plugins." do
     Pry.config.should_load_plugins = false
   end
@@ -200,12 +204,15 @@ end.process_options do |opts|
     Pry.initial_session_setup
     context = Pry.binding_for(eval(opts[:context]))
   else
-    context = Pry.top_level_binding
+    context = Pry.toplevel_binding
   end
 
   if Pry::CLI.input_args.any? && Pry::CLI.input_args != ["pry"]
     full_name = File.expand_path(Pry::CLI.input_args.first)
     Pry.load_file_through_repl(full_name)
+    if Pry.config.exit_interactive
+      Pry.toplevel_binding.pry
+    end
     exit
   end
 
diff --git a/lib/pry/config.rb b/lib/pry/config.rb
index 71c877be..e21a2577 100644
--- a/lib/pry/config.rb
+++ b/lib/pry/config.rb
@@ -69,6 +69,10 @@ class Pry
     #   Pry.config.exception_whitelist = [SystemExit, SignalException]
     attr_accessor :exception_whitelist
 
+    # Send Pry into interactive mode after finishing execution
+    # @return [Boolean]
+    attr_accessor :exit_interactive
+
     # @return [Fixnum] The number of lines of context to show before and after
     #   exceptions, etc.
     # @example