diff --git a/middleman-core/lib/middleman-core/preview_server.rb b/middleman-core/lib/middleman-core/preview_server.rb
index ed4bdb47..434860b3 100644
--- a/middleman-core/lib/middleman-core/preview_server.rb
+++ b/middleman-core/lib/middleman-core/preview_server.rb
@@ -32,6 +32,8 @@ module Middleman
         )
         
         mount_instance(app)
+
+        start_file_watcher unless options[:"disable-watcher"]
         
         @initialized ||= false
         unless @initialized
@@ -39,7 +41,9 @@ module Middleman
           
           register_signal_handlers unless ::Middleman::WINDOWS
           
-          start_file_watcher unless options[:"disable-watcher"]
+          # Save the last-used options so it may be re-used when
+          # reloading later on.
+          @last_options = options
           
           @webrick.start
         end
@@ -56,7 +60,7 @@ module Middleman
       # @return [void]
       def reload
         stop
-        start
+        start @last_options
       end
 
       # Stop the current instance, exit Webrick
@@ -79,7 +83,10 @@ module Middleman
 
           if added_and_modified.length > 0
             # See if the changed file is config.rb or lib/*.rb
-            return reload if needs_to_reload?(added_and_modified)
+            if needs_to_reload?(added_and_modified)
+              reload
+              return listener.stop
+            end
 
             # Otherwise forward to Middleman
             added_and_modified.each do |path|
@@ -89,7 +96,10 @@ module Middleman
       
           if removed.length > 0
             # See if the changed file is config.rb or lib/*.rb
-            return reload if needs_to_reload?(removed)
+            if needs_to_reload?(removed)
+              reload
+              return listener.stop
+            end
 
             # Otherwise forward to Middleman
             removed.each do |path|