diff --git a/bin/jekyll b/bin/jekyll
index 79c368d8..7556a317 100755
--- a/bin/jekyll
+++ b/bin/jekyll
@@ -6,6 +6,8 @@ $:.unshift File.join(File.dirname(__FILE__), *%w{ .. lib })
 require 'commander/import'
 require 'jekyll'
 
+Jekyll::Deprecator.process(ARGV)
+
 program :name, 'jekyll'
 program :version, Jekyll::VERSION
 program :description, 'Jekyll is a blog-aware, static site generator in Ruby'
diff --git a/jekyll.gemspec b/jekyll.gemspec
index 4bff92df..21977b6e 100644
--- a/jekyll.gemspec
+++ b/jekyll.gemspec
@@ -31,6 +31,7 @@ Gem::Specification.new do |s|
   s.add_runtime_dependency('pygments.rb', "~> 0.4.2")
   s.add_runtime_dependency('commander', "~> 4.1.3")
   s.add_runtime_dependency('safe_yaml', "~> 0.7.0")
+  s.add_runtime_dependency('colorator', "~> 0.1")
 
   s.add_development_dependency('rake', "~> 10.0.3")
   s.add_development_dependency('rdoc', "~> 3.11")
diff --git a/lib/jekyll.rb b/lib/jekyll.rb
index 291b0d1e..d8eb7a54 100644
--- a/lib/jekyll.rb
+++ b/lib/jekyll.rb
@@ -25,9 +25,12 @@ require 'English'
 require 'liquid'
 require 'maruku'
 require 'pygments'
+require 'colorator'
 
 # internal requires
 require 'jekyll/core_ext'
+require 'jekyll/logger'
+require 'jekyll/deprecator'
 require 'jekyll/configuration'
 require 'jekyll/site'
 require 'jekyll/convertible'
diff --git a/lib/jekyll/command.rb b/lib/jekyll/command.rb
index 1f305a3c..a352028b 100644
--- a/lib/jekyll/command.rb
+++ b/lib/jekyll/command.rb
@@ -18,9 +18,9 @@ module Jekyll
       site.process
     rescue Jekyll::FatalException => e
       puts
-      puts "ERROR: YOUR SITE COULD NOT BE BUILT:"
-      puts "------------------------------------"
-      puts e.message
+      Jekyll::Logger.error "ERROR:", "YOUR SITE COULD NOT BE BUILT:"
+      Jekyll::Logger.error "", "------------------------------------"
+      Jekyll::Logger.error "", e.message
       exit(1)
     end
   end
diff --git a/lib/jekyll/commands/build.rb b/lib/jekyll/commands/build.rb
index 2ee78d22..e559ff4f 100644
--- a/lib/jekyll/commands/build.rb
+++ b/lib/jekyll/commands/build.rb
@@ -17,9 +17,9 @@ module Jekyll
       def self.build(site, options)
         source = options['source']
         destination = options['destination']
-        puts  "            Source: #{source}"
-        puts  "       Destination: #{destination}"
-        print "      Generating... "
+        Jekyll::Logger.info "Source:", source
+        Jekyll::Logger.info "Destination:", destination
+        print Jekyll::Logger.formatted_topic "Generating..."
         self.process_site(site)
         puts "done."
       end
@@ -36,14 +36,14 @@ module Jekyll
         source = options['source']
         destination = options['destination']
 
-        puts " Auto-regeneration: enabled"
+        Jekyll::Logger.info "Auto-regeneration:", "enabled"
 
         dw = DirectoryWatcher.new(source, :glob => self.globs(source, destination), :pre_load => true)
         dw.interval = 1
 
         dw.add_observer do |*args|
           t = Time.now.strftime("%Y-%m-%d %H:%M:%S")
-          print "      Regenerating: #{args.size} files at #{t} "
+          print Jekyll.formatted_topic("Regenerating:") + "#{args.size} files at #{t} "
           self.process_site(site)
           puts  "...done."
         end
diff --git a/lib/jekyll/configuration.rb b/lib/jekyll/configuration.rb
index 0810276f..0dc1b63b 100644
--- a/lib/jekyll/configuration.rb
+++ b/lib/jekyll/configuration.rb
@@ -108,8 +108,8 @@ module Jekyll
     def read_config_file(file)
       configuration = dup
       next_config = YAML.safe_load_file(file)
-      raise "Configuration file: (INVALID) #{file}" if !next_config.is_a?(Hash)
-      $stdout.puts "Configuration file: #{file}"
+      raise "Configuration file: (INVALID) #{file}".yellow if !next_config.is_a?(Hash)
+      Jekyll::Logger.info "Configuration file:", file
       configuration.deep_merge(next_config)
     end
 
@@ -128,10 +128,9 @@ module Jekyll
         end
       rescue SystemCallError
         # Errno:ENOENT = file not found
-        $stderr.puts "Configuration file: none"
+        Jekyll::Logger.warn "Configuration file:", "none"
       rescue => err
-        $stderr.puts "           " +
-                     "WARNING: Error reading configuration. " +
+        Jekyll::Logger.warn "WARNING:", "Error reading configuration. " +
                      "Using defaults (and options)."
         $stderr.puts "#{err}"
       end
@@ -146,8 +145,8 @@ module Jekyll
     def backwards_compatibilize
       config = dup
       # Provide backwards-compatibility
-      if config['auto']
-        $stderr.puts "Deprecation: ".rjust(20) + "'auto' has been changed to " +
+      if config.has_key? 'auto'
+        Jekyll::Logger.warn "Deprecation:", "'auto' has been changed to " +
                    "'watch'. Please update your configuration to use 'watch'."
         config['watch'] = config['auto']
       end
diff --git a/lib/jekyll/deprecator.rb b/lib/jekyll/deprecator.rb
new file mode 100644
index 00000000..88e959b7
--- /dev/null
+++ b/lib/jekyll/deprecator.rb
@@ -0,0 +1,25 @@
+module Jekyll
+  class Deprecator
+    def self.process(args)
+      deprecation_message args, "--server", "The --server command has been replaced by the \
+                          'serve' subcommand."
+      deprecation_message args, "--no-server", "To build Jekyll without launching a server, \
+                          use the 'build' subcommand."
+      deprecation_message args, "--auto", "The switch '--auto' has been replaced with '--watch'."
+      deprecation_message args, "--no-auto", "To disable auto-replication, simply leave off \
+                          the '--watch' switch."
+      deprecation_message args, "--pygments", "The 'pygments' setting can only be set in \
+                          your config files."
+      deprecation_message args, "--paginate", "The 'paginate' setting can only be set in your \
+                          config files."
+      deprecation_message args, "--url", "The 'url' setting can only be set in your config files."
+    end
+
+    def self.deprecation_message(args, deprecated_argument, message)
+      if args.include?(deprecated_argument)
+        Jekyll::Logger.error "Deprecation:", message
+        exit(1)
+      end
+    end
+  end
+end
diff --git a/lib/jekyll/logger.rb b/lib/jekyll/logger.rb
new file mode 100644
index 00000000..74a1bdc4
--- /dev/null
+++ b/lib/jekyll/logger.rb
@@ -0,0 +1,52 @@
+module Jekyll
+  module Logger
+    # Public: Print a jekyll message to stdout
+    #
+    # topic - the topic of the message, e.g. "Configuration file", "Deprecation", etc.
+    # message - the message detail
+    #
+    # Returns nothing
+    def self.info(topic, message)
+      $stdout.puts message(topic, message)
+    end
+
+    # Public: Print a jekyll message to stderr
+    #
+    # topic - the topic of the message, e.g. "Configuration file", "Deprecation", etc.
+    # message - the message detail
+    #
+    # Returns nothing
+    def self.warn(topic, message)
+      $stderr.puts message(topic, message).yellow
+    end
+
+    # Public: Print a jekyll error message to stderr
+    #
+    # topic - the topic of the message, e.g. "Configuration file", "Deprecation", etc.
+    # message - the message detail
+    #
+    # Returns nothing
+    def self.error(topic, message)
+      $stderr.puts message(topic, message).red
+    end
+
+    # Public: Build a Jekyll topic method
+    #
+    # topic - the topic of the message, e.g. "Configuration file", "Deprecation", etc.
+    # message - the message detail
+    #
+    # Returns the formatted message
+    def self.message(topic, message)
+       formatted_topic(topic) + message.gsub(/\s+/, ' ')
+    end
+
+    # Public: Format the topic
+    #
+    # topic - the topic of the message, e.g. "Configuration file", "Deprecation", etc.
+    #
+    # Returns the formatted topic statement
+    def self.formatted_topic(topic)
+      "#{topic} ".rjust(20)
+    end
+  end
+end
diff --git a/test/test_configuration.rb b/test/test_configuration.rb
index 6eb35fc4..6e4675c6 100644
--- a/test/test_configuration.rb
+++ b/test/test_configuration.rb
@@ -64,7 +64,7 @@ class TestConfiguration < Test::Unit::TestCase
 
     should "fire warning with no _config.yml" do
       mock(YAML).safe_load_file(@path) { raise SystemCallError, "No such file or directory - #{@path}" }
-      mock($stderr).puts("Configuration file: none")
+      mock($stderr).puts("Configuration file: none".yellow)
       assert_equal Jekyll::Configuration::DEFAULTS, Jekyll.configuration({})
     end
 
@@ -76,8 +76,8 @@ class TestConfiguration < Test::Unit::TestCase
 
     should "fire warning with bad config" do
       mock(YAML).safe_load_file(@path) { Array.new }
-      mock($stderr).puts("           WARNING: Error reading configuration. Using defaults (and options).")
-      mock($stderr).puts("Configuration file: (INVALID) #{@path}")
+      mock($stderr).puts(("WARNING: ".rjust(20) + "Error reading configuration. Using defaults (and options).").yellow)
+      mock($stderr).puts("Configuration file: (INVALID) #{@path}".yellow)
       assert_equal Jekyll::Configuration::DEFAULTS, Jekyll.configuration({})
     end
   end