diff --git a/middleman-core/lib/middleman-core/application.rb b/middleman-core/lib/middleman-core/application.rb
index fe025677..0fe53343 100644
--- a/middleman-core/lib/middleman-core/application.rb
+++ b/middleman-core/lib/middleman-core/application.rb
@@ -123,7 +123,7 @@ module Middleman
     include Middleman::CoreExtensions::Extensions
     
     # Basic Rack Request Handling
-    register Middleman::CoreExtensions::Request
+    include Middleman::CoreExtensions::Request
   
     # Handle exceptions
     register Middleman::CoreExtensions::ShowExceptions
@@ -262,4 +262,4 @@ module Middleman
     end
   
   end
-end
+end
\ No newline at end of file
diff --git a/middleman-core/lib/middleman-core/cli/server.rb b/middleman-core/lib/middleman-core/cli/server.rb
index 7c8fc375..c43a507b 100644
--- a/middleman-core/lib/middleman-core/cli/server.rb
+++ b/middleman-core/lib/middleman-core/cli/server.rb
@@ -1,4 +1,4 @@
-require "middleman-core/watcher"
+require "middleman-core/preview_server"
 
 # CLI Module
 module Middleman::Cli
@@ -50,7 +50,7 @@ module Middleman::Cli
       }
       
       puts "== The Middleman is loading"
-      Middleman::Watcher.start(params)
+      Middleman::PreviewServer.start(params)
     end
   end
 
diff --git a/middleman-core/lib/middleman-core/core_extensions/extensions.rb b/middleman-core/lib/middleman-core/core_extensions/extensions.rb
index 8dc87bbc..646d4fcb 100644
--- a/middleman-core/lib/middleman-core/core_extensions/extensions.rb
+++ b/middleman-core/lib/middleman-core/core_extensions/extensions.rb
@@ -36,7 +36,7 @@ module Middleman
       # Register extension
       class << self
         # @private
-        def included(app)
+        def registered(app)
           # Using for version parsing
           require "rubygems"
 
@@ -50,6 +50,7 @@ module Middleman
           app.send :include, InstanceMethods
           app.delegate :configure, :to => :"self.class"
         end
+        alias :included :registered
       end
 
       # Class methods
diff --git a/middleman-core/lib/middleman-core/core_extensions/file_watcher.rb b/middleman-core/lib/middleman-core/core_extensions/file_watcher.rb
index 190c35f7..0e33af37 100644
--- a/middleman-core/lib/middleman-core/core_extensions/file_watcher.rb
+++ b/middleman-core/lib/middleman-core/core_extensions/file_watcher.rb
@@ -1,29 +1,40 @@
+require "find"
+require "set"
+
 # API for watching file change events
 module Middleman
   module CoreExtensions
     module FileWatcher
   
+      IGNORE_LIST = [
+        /^\.sass-cache\//,
+        /^\.git\//,
+        /^\.gitignore$/,
+        /^\.DS_Store$/,
+        /^build\//,
+        /^\.rbenv-.*$/,
+        /^Gemfile$/,
+        /^Gemfile\.lock$/,
+        /~$/
+      ]
+
       # Setup extension
       class << self
     
         # Once registered
         def registered(app)
-          require "find"
-          require "middleman-core/watcher"
-          require "set"
-          
           app.extend ClassMethods
           app.send :include, InstanceMethods
       
           # Before parsing config, load the data/ directory
           app.before_configuration do
-            data_path = File.join(self.root, self.data_dir)
-            self.files.reload_path(data_path) if File.exists?(data_path)
+            data_path = File.join(root, data_dir)
+            files.reload_path(data_path) if File.exists?(data_path)
           end
       
           # After config, load everything else
           app.ready do
-            self.files.reload_path(self.root)
+            files.reload_path(root)
           end
         end
         alias :included :registered
@@ -45,19 +56,20 @@ module Middleman
         # Access the file api
         # @return [Middleman::CoreExtensions::FileWatcher::API]
         def files
-          api = self.class.files
-          api.instance ||= self
-          api
+          @_files_api ||= API.new(self)
         end
       end
   
       # Core File Change API class
       class API
-        attr_accessor :instance, :known_paths
-    
+        
         # Initialize api and internal path cache
-        def initialize
-          self.known_paths = Set.new
+        def initialize(app)
+          @app = app
+          @known_paths = Set.new
+          
+          @_changed = []
+          @_deleted = []
         end
     
         # Add callback to be run on file change
@@ -65,7 +77,6 @@ module Middleman
         # @param [nil,Regexp] matcher A Regexp to match the change path against
         # @return [Array<Proc>]
         def changed(matcher=nil, &block)
-          @_changed ||= []
           @_changed << [block, matcher] if block_given?
           @_changed
         end
@@ -75,7 +86,6 @@ module Middleman
         # @param [nil,Regexp] matcher A Regexp to match the deleted path against
         # @return [Array<Proc>]
         def deleted(matcher=nil, &block)
-          @_deleted ||= []
           @_deleted << [block, matcher] if block_given?
           @_deleted
         end
@@ -85,8 +95,9 @@ module Middleman
         # @param [String] path The file that changed
         # @return [void]
         def did_change(path)
-          puts "== File Change: #{path}" if instance.logging? && !::Middleman::Watcher.ignore_list.any? { |r| path.match(r) }
-          self.known_paths << path
+          return if IGNORE_LIST.any? { |r| path.match(r) }
+          puts "== File Change: #{path}" if @app.logging?
+          @known_paths << path
           self.run_callbacks(path, :changed)
         end
 
@@ -95,8 +106,9 @@ module Middleman
         # @param [String] path The file that was deleted
         # @return [void]
         def did_delete(path)
-          puts "== File Deletion: #{path}" if instance.logging? && !::Middleman::Watcher.ignore_list.any? { |r| path.match(r) }
-          self.known_paths.delete(path)
+          return if IGNORE_LIST.any? { |r| path.match(r) }
+          puts "== File Deletion: #{path}" if @app.logging?
+          @known_paths.delete(path)
           self.run_callbacks(path, :deleted)
         end
     
@@ -105,13 +117,12 @@ module Middleman
         # @param [String] path The path to reload
         # @return [void]
         def reload_path(path)
-          relative_path = path.sub("#{self.instance.root}/", "")
-          subset = self.known_paths.select { |p| p.match(%r{^#{relative_path}}) }
+          relative_path = path.sub("#{@app.root}/", "")
+          subset = @known_paths.select { |p| p.match(%r{^#{relative_path}}) }
       
           Find.find(path) do |path|
             next if File.directory?(path)
-            next if Middleman::Watcher.ignore_list.any? { |r| path.match(r) }
-            relative_path = path.sub("#{self.instance.root}/", "")
+            relative_path = path.sub("#{@app.root}/", "")
             subset.delete(relative_path)
             self.did_change(relative_path)
           end if File.exists?(path)
@@ -126,13 +137,12 @@ module Middleman
         # @param [String] path The path to reload
         # @return [void]
         def find_new_files(path)
-          relative_path = path.sub("#{self.instance.root}/", "")
-          subset = self.known_paths.select { |p| p.match(%r{^#{relative_path}}) }
+          relative_path = path.sub("#{@app.root}/", "")
+          subset = @known_paths.select { |p| p.match(%r{^#{relative_path}}) }
       
           Find.find(path) do |file|
             next if File.directory?(file)
-            next if Middleman::Watcher.ignore_list.any? { |r| path.match(r) }
-            relative_path = file.sub("#{self.instance.root}/", "")
+            relative_path = file.sub("#{@app.root}/", "")
             self.did_change(relative_path) unless subset.include?(relative_path)
           end if File.exists?(path)
         end
@@ -144,12 +154,10 @@ module Middleman
         # @param [Symbol] callbacks_name The name of the callbacks method
         # @return [void]
         def run_callbacks(path, callbacks_name)
-          return if ::Middleman::Watcher.ignore_list.any? { |r| path.match(r) }
-
           self.send(callbacks_name).each do |callback, matcher|
-            next if path.match(%r{^#{self.instance.build_dir}/})
+            next if path.match(%r{^#{@app.build_dir}/})
             next unless matcher.nil? || path.match(matcher)
-            self.instance.instance_exec(path, &callback)
+            @app.instance_exec(path, &callback)
           end
         end
       end
diff --git a/middleman-core/lib/middleman-core/core_extensions/request.rb b/middleman-core/lib/middleman-core/core_extensions/request.rb
index 901cdf96..f16a408d 100644
--- a/middleman-core/lib/middleman-core/core_extensions/request.rb
+++ b/middleman-core/lib/middleman-core/core_extensions/request.rb
@@ -1,3 +1,7 @@
+# Built on Rack
+require "rack"
+require "rack/file"
+
 module Middleman
   module CoreExtensions
     
@@ -8,9 +12,6 @@ module Middleman
       class << self
         # @private
         def registered(app)
-          # Built on Rack
-          require "rack"
-          require "rack/file"
           
           # CSSPIE HTC File
           ::Rack::Mime::MIME_TYPES['.html'] = 'text/x-component'
@@ -18,7 +19,6 @@ module Middleman
           # Let's serve all HTML as UTF-8
           ::Rack::Mime::MIME_TYPES['.html'] = 'text/html;charset=utf8'
           ::Rack::Mime::MIME_TYPES['.htm'] = 'text/html;charset=utf8'
-        
           
           app.extend ClassMethods
           app.extend ServerMethods
@@ -133,30 +133,8 @@ module Middleman
           @@servercounter += 1
           const_set("MiddlemanApplication#{@@servercounter}", Class.new(Middleman::Application))
         end
-
-        # Creates a new Rack::Server
-        #
-        # @param [Hash] options to pass to Rack::Server.new
-        # @return [Rack::Server]
-        def start_server(options={})
-          opts = {
-            :Port      => options[:port] || 4567,
-            :Host      => options[:host] || "0.0.0.0",
-            :AccessLog => []
-          }
-
-          app_class = options[:app] ||= ::Middleman.server.inst
-          opts[:app] = app_class
-
-          require "webrick"
-          opts[:Logger] = WEBrick::Log::new(nil, 0) if !options[:logging]
-          opts[:server] = 'webrick'
-
-          server = ::Rack::Server.new(opts)
-          server.start
-          server
-        end
       end
+
       # Methods to be mixed-in to Middleman::Application
       module InstanceMethods
         # Backwards-compatibility with old request.path signature
@@ -212,22 +190,6 @@ module Middleman
         end
 
         def call(env)
-          # Keep `__middleman__` messaging to this thread
-          if env["PATH_INFO"] == "/__middleman__"
-            if env["REQUEST_METHOD"] == "POST"
-              req = ::Rack::Request.new(env)
-              if req.params.has_key?("change")
-                self.files.did_change(req.params["change"])
-              elsif req.params.has_key?("delete")
-                self.files.did_delete(req.params["delete"])
-              end
-            end
-            
-            res = ::Rack::Response.new
-            res.status = 200
-            return res.finish
-          end
-          
           dup.call!(env)
         end
         
diff --git a/middleman-core/lib/middleman-core/preview_server.rb b/middleman-core/lib/middleman-core/preview_server.rb
new file mode 100644
index 00000000..1ecb1783
--- /dev/null
+++ b/middleman-core/lib/middleman-core/preview_server.rb
@@ -0,0 +1,161 @@
+module Middleman
+  
+  WINDOWS = !!(RUBY_PLATFORM =~ /(mingw|bccwin|wince|mswin32)/i) unless const_defined?(:WINDOWS)
+
+  module PreviewServer
+    
+    DEFAULT_PORT = 4567
+    
+    class << self
+      
+      # Start an instance of Middleman::Application
+      # @return [void]
+      def start(options={})
+        require "webrick"
+        
+        @first_run ||= true
+        
+        app = ::Middleman::Application.server.inst do
+          if options[:environment]
+            set :environment, options[:environment]
+          end
+          
+          if options[:debug]
+            set :logging, true
+          end
+        end
+    
+        puts "== The Middleman is standing watch on port #{options[:port]||4567}"
+          
+        @webrick_is_running ||= false
+        @webrick ||= setup_webrick(
+          options[:host]  || "0.0.0.0",
+          options[:port]  || DEFAULT_PORT,
+          options[:debug] || false
+        )
+        
+        mount_instance(app)
+        
+        if @first_run
+          @first_run = false
+          
+          register_signal_handlers unless ::Middleman::WINDOWS
+          
+          start_file_watcher unless options[:"disable-watcher"]
+          
+          @webrick.start
+        end
+      end
+
+      # Detach the current Middleman::Application instance
+      # @return [void]
+      def stop
+        puts "== The Middleman is shutting down"
+        unmount_instance
+      end
+    
+      # Simply stop, then start the server
+      # @return [void]
+      def reload
+        stop
+        start
+      end
+
+      # Stop the current instance, exit Webrick
+      # @return [void]
+      def shutdown
+        stop
+        @webrick.shutdown
+      end
+      
+    private
+      
+      def start_file_watcher
+        preview_server = self
+
+        # Watcher Library
+        require "listen"
+    
+        listener = Listen.to(Dir.pwd, :relative_paths => true)
+      
+        listener.change do |modified, added, removed|
+          added_and_modified = (modified + added)
+
+          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)
+
+            # Otherwise forward to Middleman
+            paths.each do |path|
+              @app.files.did_change(path)
+            end
+          end
+      
+          if removed.length > 0
+            # See if the changed file is config.rb or lib/*.rb
+            return reload if needs_to_reload?(removed)
+
+            # Otherwise forward to Middleman
+            removed.each do |path|
+              @app.files.did_delete(path)
+            end
+          end
+        end
+    
+        # Don't block this thread
+        listener.start(false)
+      end
+      
+      # Trap the interupt signal and shut down smoothly
+      # @return [void]
+      def register_signal_handlers
+        trap("INT")  { shutdown }
+        trap("TERM") { shutdown }
+        trap("QUIT") { shutdown }
+      end
+      
+      # Initialize webrick 
+      # @return [void]
+      def setup_webrick(host, port, is_logging)
+        @host = host
+        @port = port
+        
+        http_opts = {
+          :BindAddress => @host,
+          :Port        => @port,
+          :AccessLog   => []
+        }
+        
+        unless is_logging
+          http_opts[:Logger] = ::WEBrick::Log::new(nil, 0)
+        end
+      
+        ::WEBrick::HTTPServer.new(http_opts)
+      end
+    
+      # Attach a new Middleman::Application instance
+      # @param [Middleman::Application] app
+      # @return [void]
+      def mount_instance(app)
+        @app = app
+        @webrick.mount "/", ::Rack::Handler::WEBrick, @app.class.to_rack_app
+      end
+    
+      # Detach the current Middleman::Application instance
+      # @return [void]
+      def unmount_instance
+        @webrick.unmount "/"
+        @app = nil
+      end
+
+      # Whether the passed files are config.rb, lib/*.rb or helpers
+      # @param [Array<String>] paths Array of paths to check
+      # @return [Boolean] Whether the server needs to reload
+      def needs_to_reload?(paths)
+        paths.any? do |path|
+          path.match(%{^config\.rb}) || path.match(%r{^lib/^[^\.](.*)\.rb$}) || path.match(%r{^helpers/^[^\.](.*)_helper\.rb$})
+        end
+      end
+    end
+  end
+end
\ No newline at end of file
diff --git a/middleman-core/lib/middleman-core/watcher.rb b/middleman-core/lib/middleman-core/watcher.rb
deleted file mode 100644
index 18ae6346..00000000
--- a/middleman-core/lib/middleman-core/watcher.rb
+++ /dev/null
@@ -1,149 +0,0 @@
-# File changes are forwarded to the currently running app via HTTP
-require "net/http"
-require "fileutils"
-
-module Middleman
-  WINDOWS = !!(RUBY_PLATFORM =~ /(mingw|bccwin|wince|mswin32)/i) unless const_defined?(:WINDOWS)
-end
-
-module Middleman
-  class Watcher
-    class << self
-      attr_accessor :singleton
-      
-      def start(options)
-        self.singleton = new(options)
-        self.singleton.watch! unless options[:"disable-watcher"]
-        self.singleton.start
-      end
-      
-      def ignore_list
-        [
-          /^\.sass-cache\//,
-          /^\.git\//,
-          /^\.gitignore$/,
-          /^\.DS_Store$/,
-          /^build\//,
-          /^\.rbenv-.*$/,
-          /^Gemfile$/,
-          /^Gemfile\.lock$/,
-          /~$/
-        ]
-      end
-    end
-    
-    def initialize(options)
-      @options = options
-      register_signal_handlers unless ::Middleman::WINDOWS
-    end
-    
-    def watch!
-      local = self
-
-      # Watcher Library
-      require "listen"
-      
-      listener = Listen.to(Dir.pwd, :relative_paths => true)
-      listener.change do |modified, added, removed|
-        added_and_modified = modified + added
-
-        if added_and_modified.length > 0
-          local.run_on_change(added_and_modified)
-        end
-        
-        if removed.length > 0
-          local.run_on_deletion(removed)
-        end
-      end
-      # Don't block this thread
-      listener.start(false)
-    end
-    
-    # Start an instance of Middleman::Application
-    # @return [void]
-    def start
-      env = (@options[:environment] || "development").to_sym
-      is_logging = @options.has_key?(:debug) && @options[:debug]
-      
-      app = ::Middleman::Application.server.inst do
-        set :environment, env
-        set :logging, is_logging
-      end
-      
-      app_rack = app.class.to_rack_app
-      
-      opts = @options.dup
-      opts[:app] = app_rack
-      opts[:logging] = is_logging
-      puts "== The Middleman is standing watch on port #{opts[:port]||4567}"
-      ::Middleman::Application.start_server(opts)
-    end
-    
-    # Stop the forked Middleman
-    # @return [void]
-    def stop
-      puts "== The Middleman is shutting down"
-      # TODO: Figure out some way to actually unload the whole thing
-      #       or maybe just re-exec this same thing
-    end
-    
-    # Simply stop, then start
-    # @return [void]
-    def reload
-      stop
-      start
-    end
-    
-    # What to do on file change
-    # @param [Array<String>] paths Array of paths that changed
-    # @return [void]
-    def run_on_change(paths)
-      # See if the changed file is config.rb or lib/*.rb
-      return reload if needs_to_reload?(paths)
-      
-      # Otherwise forward to Middleman
-      paths.each do |path|
-        tell_server(:change => path) unless self.class.ignore_list.any? { |r| path.match(r) }
-      end
-    end
-
-    # What to do on file deletion
-    # @param [Array<String>] paths Array of paths that were removed
-    # @return [void]
-    def run_on_deletion(paths)
-      # See if the changed file is config.rb or lib/*.rb
-      return reload if needs_to_reload?(paths)
-      
-      # Otherwise forward to Middleman
-      paths.each do |path|
-        tell_server(:delete => path) unless self.class.ignore_list.any? { |r| path.match(r) }
-      end
-    end
-    
-  private
-    # Trap the interupt signal and shut down FSSM (and thus the server) smoothly
-    def register_signal_handlers
-      trap("INT")  { stop; exit(0) }
-      trap("TERM") { stop }
-      trap("QUIT") { stop; exit(0) }
-    end
-
-    # Whether the passed files are config.rb, lib/*.rb or helpers
-    # @param [Array<String>] paths Array of paths to check
-    # @return [Boolean] Whether the server needs to reload
-    def needs_to_reload?(paths)
-      return false # disable reloading for now
-      paths.any? do |path|
-        path.match(%{^config\.rb}) || path.match(%r{^lib/^[^\.](.*)\.rb$}) || path.match(%r{^helpers/^[^\.](.*)_helper\.rb$})
-      end
-    end
-  
-    # Send a message to the running server
-    # @param [Hash] params Keys to be hashed and sent to server
-    # @return [void]
-    def tell_server(params={})
-      uri = URI.parse("http://#{@options[:host]}:#{@options[:port]}/__middleman__")
-      Net::HTTP.post_form(uri, {}.merge(params))
-    end
-  end
-end