diff --git a/middleman-core/lib/middleman-core/application.rb b/middleman-core/lib/middleman-core/application.rb
index 85b4a559..dda5e265 100644
--- a/middleman-core/lib/middleman-core/application.rb
+++ b/middleman-core/lib/middleman-core/application.rb
@@ -25,6 +25,15 @@ require 'middleman-core/config_context'
 require 'middleman-core/file_renderer'
 require 'middleman-core/template_renderer'
 
+# Rack Request
+require 'middleman-core/core_extensions/request'
+
+# Custom Extension API and config.rb handling
+require 'middleman-core/core_extensions/extensions'
+
+# Catch and show exceptions at the Rack level
+require 'middleman-core/core_extensions/show_exceptions'
+
 # Core Middleman Class
 module Middleman
   class Application
@@ -168,7 +177,7 @@ module Middleman
     delegate :link_to, :image_tag, :asset_path, to: :generic_template_context
 
     # Initialize the Middleman project
-    def initialize(&block)
+    def initialize
       @template_context_class = Class.new(Middleman::TemplateContext)
       @generic_template_context = @template_context_class.new(self)
       @config_context = ConfigContext.new(self, @template_context_class)
@@ -193,19 +202,6 @@ module Middleman
 
       config[:source] = ENV['MM_SOURCE'] if ENV['MM_SOURCE']
 
-      # Built-in extensions
-      activate :default_helpers
-      activate :lorem
-
-      begin
-        activate :compass
-      rescue LoadError
-        # Compass is not available, don't complain about it
-      end
-
-      # Evaluate a passed block if given
-      @config_context.instance_exec(&block) if block_given?
-
       super
     end
 
diff --git a/middleman-core/lib/middleman-core/config_context.rb b/middleman-core/lib/middleman-core/config_context.rb
index 3d46b88b..ff5ffa76 100644
--- a/middleman-core/lib/middleman-core/config_context.rb
+++ b/middleman-core/lib/middleman-core/config_context.rb
@@ -1,3 +1,5 @@
+require 'middleman-core/core_extensions/routing'
+
 module Middleman
   class ConfigContext
     # page routing
diff --git a/middleman-core/lib/middleman-core/core_extensions.rb b/middleman-core/lib/middleman-core/core_extensions.rb
index 340ca2fd..179b83bb 100644
--- a/middleman-core/lib/middleman-core/core_extensions.rb
+++ b/middleman-core/lib/middleman-core/core_extensions.rb
@@ -1,12 +1,6 @@
-# Rack Request
-require 'middleman-core/core_extensions/request'
-
 # File Change Notifier
 require 'middleman-core/core_extensions/file_watcher'
 
-# Custom Feature API
-require 'middleman-core/core_extensions/extensions'
-
 # Data looks at the data/ folder for YAML files and makes them available
 # to dynamic requests.
 require 'middleman-core/core_extensions/data'
@@ -23,22 +17,18 @@ require 'middleman-core/core_extensions/external_helpers'
 # Extended version of Padrino's rendering
 require 'middleman-core/core_extensions/rendering'
 
-# Pass custom options to views
-require 'middleman-core/core_extensions/routing'
-
-# Catch and show exceptions at the Rack level
-require 'middleman-core/core_extensions/show_exceptions'
-
 # Setup default helpers
-Middleman::Extensions.register :default_helpers do
+Middleman::Extensions.register :default_helpers, auto_activate_before_configuration: true do
   require 'middleman-core/core_extensions/default_helpers'
   Middleman::CoreExtensions::DefaultHelpers
 end
 
 # Compass framework
-Middleman::Extensions.register :compass do
+begin
   require 'middleman-core/core_extensions/compass'
-  Middleman::CoreExtensions::Compass
+  Middleman::Extensions.register :compass, Middleman::CoreExtensions::Compass, auto_activate_before_configuration: true
+rescue LoadError
+  # Compass is not available, don't complain about it
 end
 
 ###
@@ -105,7 +95,7 @@ end
 
 # Lorem provides a handful of helpful prototyping methods to generate
 # words, paragraphs, fake images, names and email addresses.
-Middleman::Extensions.register :lorem do
+Middleman::Extensions.register :lorem, auto_activate_before_configuration: true do
   require 'middleman-core/extensions/lorem'
   Middleman::Extensions::Lorem
 end
diff --git a/middleman-core/lib/middleman-core/core_extensions/extensions.rb b/middleman-core/lib/middleman-core/core_extensions/extensions.rb
index 42d12465..ea91c8cf 100644
--- a/middleman-core/lib/middleman-core/core_extensions/extensions.rb
+++ b/middleman-core/lib/middleman-core/core_extensions/extensions.rb
@@ -76,7 +76,7 @@ module Middleman
       end
 
       # Override application initialization to load `config.rb` and to call lifecycle hooks.
-      def initialize
+      def initialize(&block)
         super
 
         self.class.inst = self
@@ -99,6 +99,9 @@ module Middleman
           end
         end
 
+        # Evaluate a passed block if given
+        config_context.instance_exec(&block) if block_given?
+
         run_hook :initialized
 
         run_hook :before_configuration
diff --git a/middleman-core/lib/middleman-core/core_extensions/rendering.rb b/middleman-core/lib/middleman-core/core_extensions/rendering.rb
index 9b3c492a..53f72265 100644
--- a/middleman-core/lib/middleman-core/core_extensions/rendering.rb
+++ b/middleman-core/lib/middleman-core/core_extensions/rendering.rb
@@ -1,7 +1,6 @@
 require 'middleman-core/template_context'
 
 # Rendering extension
-# rubocop:disable UnderscorePrefixedVariableName
 module Middleman
   module CoreExtensions
     module Rendering