diff --git a/bin/mm-server b/bin/mm-server
index e4f97307..399b9d46 100755
--- a/bin/mm-server
+++ b/bin/mm-server
@@ -5,10 +5,8 @@ require 'optparse'
 # Require Middleman
 require File.join(File.dirname(__FILE__), '..', 'lib', 'middleman')
 
-sandboxed_server = Middleman.server
-
 env = ENV['MM_ENV'] || ENV['RACK_ENV'] || 'development'
-options = { :Port => 4567, :AccessLog => [] }
+options = {}
 
 # TODO: Switch to Thor
 OptionParser.new { |opts|
@@ -16,60 +14,26 @@ OptionParser.new { |opts|
   opts.separator ""
   opts.separator "Rack options:"
   opts.on("-p", "--port PORT", "use PORT (default: 4567)") { |port|
-    options[:Port] = port
+    options[:port] = port
   }
   opts.on("-E", "--env ENVIRONMENT", "use ENVIRONMENT for defaults (default: development)") { |e|
     env = e
   }
-  opts.on("--debug", "Debug mode") {
-    sandboxed_server.set :logging, true
-  }
 
   opts.parse! ARGV
 }
 
 ENV['RACK_ENV'] = env
 
-@current_path = Dir.pwd
-@path_parts = @current_path.split("/")
-@found_root = false
-
-while (!@found_root && (@path_parts.length > 0))
-  @current_path = File.join(*@path_parts)
-  
-  source_folder = File.join(@current_path, "source")
-  
-  if File.exists?(source_folder)
-    @found_root = true
-    next
-  end
-  
-  @path_parts.pop
-end
-
-if !@found_root
-  $stderr.puts "== Error: Could not find a Middleman project structure, perhaps you are in the wrong folder?"
-  exit
-end
-
-# If the old init.rb exists, issue warning
-old_config = File.join(@current_path, "init.rb")
-if File.exists? old_config
-  $stderr.puts "== Error: The init.rb file (deprecated) needs to be be renamed to config.rb"
+if !File.exists?("config.rb")
+  $stderr.puts "== Error: Could not find a Middleman project config, perhaps you are in the wrong folder?"
   exit
 end
 
 # If the old directories exists, use it, but issue warning
-old_views = File.join(@current_path, "views")
-old_public = File.join(@current_path, "public")
-if File.exists?(old_views) || File.exists?(old_public)
+if File.exists?("views") || File.exists?("public")
   $stderr.puts "== Error: The views and public folders are have been combined. Create a new 'source' folder, add the contents of views and public to it and then remove the empty views and public folders."
   exit
 end
 
-sandboxed_server.set :root, @current_path
-options[:app]    = sandboxed_server.new
-# options[:server] = 'webrick'
-
-puts "== The Middleman is standing watch on port #{options[:Port]}"
-Rack::Server.new(options).start
+Middleman::Guard.start(options)
\ No newline at end of file
diff --git a/lib/middleman.rb b/lib/middleman.rb
index 737766f2..54e81be9 100755
--- a/lib/middleman.rb
+++ b/lib/middleman.rb
@@ -66,6 +66,7 @@ module Middleman
   # Auto-load modules on-demand
   autoload :Base,      "middleman/base"
   autoload :Builder,   "middleman/builder"
+  autoload :Guard,     "middleman/guard"
   
   # Custom Renderers
   module Renderers
diff --git a/lib/middleman/guard.rb b/lib/middleman/guard.rb
new file mode 100644
index 00000000..423ecabe
--- /dev/null
+++ b/lib/middleman/guard.rb
@@ -0,0 +1,57 @@
+require "guard"
+require "guard/guard"
+
+module Middleman::Guard
+  def self.start(options={})
+    options_hash = ""
+    options.each do |k,v|
+      options_hash << ", :#{k} => '#{v}'"
+    end
+    
+    ::Guard.start({
+      :guardfile_contents => %Q{
+        guard 'MiddlemanServer'#{options_hash} do 
+          watch("config.rb")
+        end
+      }
+    })
+  end
+end
+
+module Guard
+  class MiddlemanServer < Guard
+    def initialize(watchers = [], options = {})
+      super
+      @options = {
+        :port => '4567'
+      }.update(options)
+    end
+    
+    def start
+      server_start
+    end
+  
+    def run_on_change(paths)
+      server_stop
+      server_start
+    end
+
+  private
+    def server_start
+      puts "== The Middleman is standing watch on port #{@options[:port]}"
+      @server_options = { :Port => @options[:port], :AccessLog => [] }
+      @server_job = fork do
+        @server_options[:app] = Middleman.server.new
+        ::Rack::Server.new(@server_options).start
+      end
+    end
+  
+    def server_stop
+      puts "== The Middleman is shutting down"
+      Process.kill("KILL", @server_job)
+      Process.wait @server_job
+      @server_job = nil
+      @server_options[:app] = nil
+    end
+  end
+end
\ No newline at end of file
diff --git a/middleman.gemspec b/middleman.gemspec
index 9ae495ab..f75143d8 100644
--- a/middleman.gemspec
+++ b/middleman.gemspec
@@ -34,6 +34,8 @@ Gem::Specification.new do |s|
   s.add_runtime_dependency("compass", ["~> 0.11.3"])
   s.add_runtime_dependency("sprockets", ["2.0.0.beta.10"])
   s.add_runtime_dependency("httparty", ["~> 0.7.0"])
+  s.add_runtime_dependency("guard", [">= 0"])
+  s.add_runtime_dependency("guard-livereload", [">= 0"])
   s.add_development_dependency("coffee-filter", ["~> 0.1.1"])
   s.add_development_dependency("cucumber", ["~> 0.10.0"])
   s.add_development_dependency("rake", ["0.8.7"])