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@@ -849,15 +849,13 @@ module Sinatra
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     # handlers as values.
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     attr_reader :filters
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-    # Truthful when the application is in the process of being reloaded.
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-    attr_reader :reloading
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-
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     # Array of objects to clear during reload. The objects in this array
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     # must respond to :clear.
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     attr_reader :clearables
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-    # Application options.
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-    attr_accessor :options
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+    # Object including open attribute methods for modifying Application
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+    # configuration.
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+    attr_reader :options
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     # List of methods available from top-level scope. When invoked from
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     # top-level the method is forwarded to the default application
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@@ -865,11 +863,21 @@ module Sinatra
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     FORWARD_METHODS = %w[
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       get put post delete head
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       template layout before error not_found
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+      configures configure
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     ]
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+    # Hash of default application configuration options. When a new
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+    # Application is created, the #options object takes its initial values
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+    # from here.
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+    #
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+    # Changes to the default_options Hash effect only Application objects
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+    # created after the changes are made. For this reason, modifications to
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+    # the default_options Hash typically occur at the very beginning of a
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+    # file, before any DSL related functions are invoked.
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     def self.default_options
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+      return @default_options unless @default_options.nil?
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       root = File.expand_path(File.dirname($0))
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-      @@default_options ||= {
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+      @default_options = {
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         :run => true,
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         :port => 4567,
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         :env => :development,
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@@ -879,17 +887,15 @@ module Sinatra
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         :sessions => false,
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         :logging => true
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       }
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-    end
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-    
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-    def default_options
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-      self.class.default_options
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+      load_default_options_from_command_line!
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+      @default_options
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     end
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-    
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-    ##
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-    # Load all options given on the command line
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+    # Search ARGV for command line arguments and update the
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+    # Sinatra::default_options Hash accordingly. This method is
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+    # invoked the first time the default_options Hash is accessed.
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     # NOTE:  Ignores --name so unit/spec tests can run individually
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-    def load_options!
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+    def self.load_default_options_from_command_line! #:nodoc:
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       require 'optparse'
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       OptionParser.new do |op|
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         op.on('-p port') { |port| default_options[:port] = port }
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@@ -907,16 +913,37 @@ module Sinatra
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     end
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     def initialize
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+      @reloading = false
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       @clearables = [
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         @events = Hash.new { |hash, key| hash[key] = [] },
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         @errors = Hash.new,
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         @filters = Hash.new { |hash, key| hash[key] = [] },
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         @templates = Hash.new
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       ]
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-      load_options!
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+      @options = OpenStruct.new(self.class.default_options)
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       load_default_events!
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     end
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+    # Determine whether the application is in the process of being
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+    # reloaded.
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+    def reloading?
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+      @reloading == true
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+    end
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+
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+    # Yield to the block for configuration if the current environment
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+    # matches any included in the +envs+ list. Always yield to the block
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+    # when no environment is specified.
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+    #
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+    # NOTE: configuration blocks are not executed during reloads.
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+    def configures(*envs, &b)
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+      return if reloading?
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+      return unless envs.empty? || envs.include?(options.env)
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+      yield self
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+    end
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+
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+    alias :configure :configures
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+
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+
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     # Define an event handler for the given request method and path
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     # spec. The block is executed when a request matches the method
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     # and spec.
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@@ -1036,10 +1063,6 @@ module Sinatra
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         errors[NotFound].invoke(request)
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     end
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-    def options
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-      @options ||= OpenStruct.new(default_options)
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-    end
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-    
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     def development?
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       options.env == :development
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     end
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@@ -1052,7 +1075,7 @@ module Sinatra
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       @reloading = false
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       Environment.setup!
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     end
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-    
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+
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     def mutex
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       @@mutex ||= Mutex.new
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     end
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@@ -1236,16 +1259,8 @@ def use_in_file_templates!
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   end
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 end
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-def configures(*envs, &b)
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-  yield if  !Sinatra.application.reloading && 
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-            (envs.include?(Sinatra.application.options.env) ||
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-            envs.empty?)
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-end
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-alias :configure :configures
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-
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 def set_options(opts)
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   Sinatra::Application.default_options.merge!(opts)
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-  Sinatra.application.options = nil
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 end
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 def set_option(key, value)

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@@ -10,4 +10,4 @@ Sinatra::Application.default_options.merge!(
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   :logging => false
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 )
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-Sinatra.application.options = nil
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+Sinatra.application = nil

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@@ -97,7 +97,38 @@ context "An app returns" do
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   end
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 end
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-  
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+
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+context "Application#configure blocks" do
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+
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+  setup do
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+    Sinatra.application = nil
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+  end
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+
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+  specify "run when no environment specified" do
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+    ref = false
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+    configure { ref = true }
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+    ref.should.equal true
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+  end
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+
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+  specify "run when matching environment specified" do
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+    ref = false
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+    configure(:test) { ref = true }
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+    ref.should.equal true
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+  end
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+
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+  specify "do not run when no matching environment specified" do
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+    configure(:foo) { flunk "block should not have been executed" }
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+    configure(:development, :production, :foo) { flunk "block should not have been executed" }
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+  end
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+
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+  specify "accept multiple environments" do
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+    ref = false
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+    configure(:foo, :test, :bar) { ref = true }
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+    ref.should.equal true
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+  end
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+
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+end
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+
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 context "Events in an app" do
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   setup do