diff --git a/middleman-cli/features/support/env.rb b/middleman-cli/features/support/env.rb
index 3e14c957..64cfaef1 100644
--- a/middleman-cli/features/support/env.rb
+++ b/middleman-cli/features/support/env.rb
@@ -1,6 +1,8 @@
 ENV['TEST'] = 'true'
 
 require 'backports/latest'
+require 'active_support/all'
+
 require 'sassc'
 
 require 'simplecov'
diff --git a/middleman-core/features/incremental_builds.feature b/middleman-core/features/incremental_builds.feature
index 5d1c9964..41264379 100644
--- a/middleman-core/features/incremental_builds.feature
+++ b/middleman-core/features/incremental_builds.feature
@@ -591,9 +591,9 @@ Feature: Incremental builds
     When a file named "source/roles/data.json.erb" with:
       """
       {
-        "roles": <%= data.roles.select(&:salary).to_json %>
+        "roles": <%= data.roles.select(&:salary).to_json %>,
+        "roles2": <%= data.roles.first.as_json %>
       }
       """
-    Then build the app tracking dependencies
-    Then there are "1" files which are created
-    # with depth "1"
\ No newline at end of file
+    Then build the app tracking dependencies with depth "1"
+    Then there are "1" files which are created
\ No newline at end of file
diff --git a/middleman-core/features/support/env.rb b/middleman-core/features/support/env.rb
index ac7e5491..127aa111 100644
--- a/middleman-core/features/support/env.rb
+++ b/middleman-core/features/support/env.rb
@@ -1,6 +1,8 @@
 ENV['TEST'] = 'true'
 
 require 'backports/latest'
+require 'active_support/all'
+
 require 'sassc'
 
 require 'simplecov'
diff --git a/middleman-core/lib/middleman-core.rb b/middleman-core/lib/middleman-core.rb
index a83a8d94..12c413f8 100644
--- a/middleman-core/lib/middleman-core.rb
+++ b/middleman-core/lib/middleman-core.rb
@@ -3,6 +3,7 @@ libdir = __dir__
 $LOAD_PATH.unshift(libdir) unless $LOAD_PATH.include?(libdir)
 
 require 'backports/latest'
+require 'active_support/all'
 
 # Top-level Middleman namespace
 module Middleman
diff --git a/middleman-core/lib/middleman-core/application.rb b/middleman-core/lib/middleman-core/application.rb
index d1c6b76e..51dd8225 100644
--- a/middleman-core/lib/middleman-core/application.rb
+++ b/middleman-core/lib/middleman-core/application.rb
@@ -1,4 +1,3 @@
-require 'active_support/core_ext/integer/inflections'
 require 'hamster'
 require 'middleman-core/contracts'
 require 'middleman-core/callback_manager'
diff --git a/middleman-core/lib/middleman-core/core_extensions/collections/pagination.rb b/middleman-core/lib/middleman-core/core_extensions/collections/pagination.rb
index 4d96aa77..5cce42ea 100644
--- a/middleman-core/lib/middleman-core/core_extensions/collections/pagination.rb
+++ b/middleman-core/lib/middleman-core/core_extensions/collections/pagination.rb
@@ -1,4 +1,3 @@
-require 'active_support/core_ext/object/deep_dup'
 require 'middleman-core/util'
 
 module Middleman
diff --git a/middleman-core/lib/middleman-core/core_extensions/data/proxies/array.rb b/middleman-core/lib/middleman-core/core_extensions/data/proxies/array.rb
index 2115713b..0f575561 100644
--- a/middleman-core/lib/middleman-core/core_extensions/data/proxies/array.rb
+++ b/middleman-core/lib/middleman-core/core_extensions/data/proxies/array.rb
@@ -8,6 +8,10 @@ module Middleman
         class ArrayProxy < BaseProxy
           WRAPPED_LIST_METHODS = Set.new %i[each each_with_index select sort shuffle reverse rotate sample]
 
+          def respond_to_missing?(name, *)
+            self.class.const_get(:WRAPPED_LIST_METHODS).include?(name) || super
+          end
+
           def method_missing(name, *args, &block)
             if self.class.const_get(:WRAPPED_LIST_METHODS).include?(name)
               log_access(:__full_access__)
@@ -53,16 +57,6 @@ module Middleman
             end
           end
 
-          def to_s
-            log_access(:__full_access__)
-            @data.to_s
-          end
-
-          def to_json(*args)
-            log_access(:__full_access__)
-            @data.to_a.to_json(*args)
-          end
-
           private
 
           def wrapped_array
diff --git a/middleman-core/lib/middleman-core/core_extensions/data/proxies/base.rb b/middleman-core/lib/middleman-core/core_extensions/data/proxies/base.rb
index a4381118..f3c99fc7 100644
--- a/middleman-core/lib/middleman-core/core_extensions/data/proxies/base.rb
+++ b/middleman-core/lib/middleman-core/core_extensions/data/proxies/base.rb
@@ -20,6 +20,10 @@ module Middleman
             @accessed_keys = ::Hamster::Set.new
           end
 
+          def respond_to_missing?(name, *)
+            @data.respond_to?(name) || super
+          end
+
           def method_missing(name, *args, &block)
             if @data.respond_to?(name)
               log_access(:__full_access__)
@@ -40,6 +44,11 @@ module Middleman
             @parent = new_parent
           end
 
+          def as_json(*args)
+            log_access(:__full_access__)
+            @data.as_json(*args)
+          end
+
           protected
 
           def log_access(key)
diff --git a/middleman-core/lib/middleman-core/core_extensions/data/proxies/hash.rb b/middleman-core/lib/middleman-core/core_extensions/data/proxies/hash.rb
index ccd3641a..cb3be832 100644
--- a/middleman-core/lib/middleman-core/core_extensions/data/proxies/hash.rb
+++ b/middleman-core/lib/middleman-core/core_extensions/data/proxies/hash.rb
@@ -14,6 +14,10 @@ module Middleman
           end
           alias get []
 
+          def respond_to_missing?(name, *)
+            @data.key?(name) || super
+          end
+
           def method_missing(name, *_args)
             return self[name] if @data.key?(name)
 
@@ -21,16 +25,6 @@ module Middleman
           rescue NoMethodError
             nil
           end
-
-          def to_s
-            log_access(:__full_access__)
-            @data.to_s
-          end
-
-          def to_json(*args)
-            log_access(:__full_access__)
-            @data.to_h.to_json(*args)
-          end
         end
       end
     end
diff --git a/middleman-core/lib/middleman-core/core_extensions/default_helpers.rb b/middleman-core/lib/middleman-core/core_extensions/default_helpers.rb
index 91321a16..ef5fada9 100644
--- a/middleman-core/lib/middleman-core/core_extensions/default_helpers.rb
+++ b/middleman-core/lib/middleman-core/core_extensions/default_helpers.rb
@@ -23,8 +23,6 @@ class Middleman::CoreExtensions::DefaultHelpers < ::Middleman::Extension
   def initialize(app, options_hash = ::Middleman::EMPTY_HASH, &block)
     super
 
-    require 'active_support/core_ext/object/to_query'
-
     ::Middleman::TemplateContext.send :include, ::Padrino::Helpers::OutputHelpers
     ::Middleman::TemplateContext.send :include, ::Padrino::Helpers::TagHelpers
     ::Middleman::TemplateContext.send :include, ::Padrino::Helpers::AssetTagHelpers
@@ -47,7 +45,7 @@ class Middleman::CoreExtensions::DefaultHelpers < ::Middleman::Extension
 
       options    = parse_data_options(name, options)
       attributes = tag_attributes(options)
-      output = ActiveSupport::SafeBuffer.new
+      output = ::ActiveSupport::SafeBuffer.new
       output.safe_concat "<#{name}#{attributes}>"
 
       if content.respond_to?(:each) && !content.is_a?(String)
diff --git a/middleman-core/lib/middleman-core/core_extensions/front_matter.rb b/middleman-core/lib/middleman-core/core_extensions/front_matter.rb
index 414574a3..9804751f 100644
--- a/middleman-core/lib/middleman-core/core_extensions/front_matter.rb
+++ b/middleman-core/lib/middleman-core/core_extensions/front_matter.rb
@@ -4,8 +4,6 @@ require 'pathname'
 # DbC
 require 'middleman-core/contracts'
 
-require 'active_support/core_ext/hash/keys'
-
 require 'middleman-core/util/data'
 
 # Extensions namespace
diff --git a/middleman-core/lib/middleman-core/extension.rb b/middleman-core/lib/middleman-core/extension.rb
index 43d98690..90ccf81d 100644
--- a/middleman-core/lib/middleman-core/extension.rb
+++ b/middleman-core/lib/middleman-core/extension.rb
@@ -1,6 +1,5 @@
 require 'forwardable'
 require 'memoist'
-require 'active_support/core_ext/class/attribute'
 require 'middleman-core/configuration'
 require 'middleman-core/contracts'
 
diff --git a/middleman-core/lib/middleman-core/extensions/minify_css.rb b/middleman-core/lib/middleman-core/extensions/minify_css.rb
index 2859d784..64801c6e 100644
--- a/middleman-core/lib/middleman-core/extensions/minify_css.rb
+++ b/middleman-core/lib/middleman-core/extensions/minify_css.rb
@@ -1,4 +1,3 @@
-require 'active_support/core_ext/object/try'
 require 'memoist'
 require 'middleman-core/contracts'
 require 'rack/mime'
diff --git a/middleman-core/lib/middleman-core/extensions/minify_javascript.rb b/middleman-core/lib/middleman-core/extensions/minify_javascript.rb
index acfa3513..b7432f16 100644
--- a/middleman-core/lib/middleman-core/extensions/minify_javascript.rb
+++ b/middleman-core/lib/middleman-core/extensions/minify_javascript.rb
@@ -1,4 +1,3 @@
-require 'active_support/core_ext/object/try'
 require 'middleman-core/contracts'
 require 'memoist'
 
diff --git a/middleman-core/lib/middleman-core/file_renderer.rb b/middleman-core/lib/middleman-core/file_renderer.rb
index 3b85738f..a6e44435 100644
--- a/middleman-core/lib/middleman-core/file_renderer.rb
+++ b/middleman-core/lib/middleman-core/file_renderer.rb
@@ -1,7 +1,5 @@
 require 'tilt'
 require 'hamster'
-require 'active_support/core_ext/string/output_safety'
-require 'active_support/core_ext/module/delegation'
 require 'middleman-core/contracts'
 require 'middleman-core/dependencies/vertices/vertex'
 
diff --git a/middleman-core/lib/middleman-core/logger.rb b/middleman-core/lib/middleman-core/logger.rb
index d8e06bbe..989656b5 100644
--- a/middleman-core/lib/middleman-core/logger.rb
+++ b/middleman-core/lib/middleman-core/logger.rb
@@ -1,9 +1,7 @@
 # Use the Ruby/Rails logger
-require 'active_support/notifications'
-require 'active_support/logger'
 module Middleman
   # The Middleman Logger
-  class Logger < ActiveSupport::Logger
+  class Logger < ::ActiveSupport::Logger
     def self.singleton(*args)
       if !@_logger || !args.empty?
         args = [0, false, args.first] if args.length == 1 && (args.first.is_a?(::String) || args.first.respond_to?(:write))
diff --git a/middleman-core/lib/middleman-core/preview_server/information.rb b/middleman-core/lib/middleman-core/preview_server/information.rb
index 7c03b449..1e9a8236 100644
--- a/middleman-core/lib/middleman-core/preview_server/information.rb
+++ b/middleman-core/lib/middleman-core/preview_server/information.rb
@@ -1,5 +1,4 @@
 require 'ipaddr'
-require 'active_support/core_ext/object/blank'
 require 'middleman-core/preview_server/checks'
 require 'middleman-core/preview_server/server_hostname'
 require 'middleman-core/preview_server/server_ip_address'
diff --git a/middleman-core/lib/middleman-core/renderers/erb.rb b/middleman-core/lib/middleman-core/renderers/erb.rb
index 5305406f..0d541db4 100644
--- a/middleman-core/lib/middleman-core/renderers/erb.rb
+++ b/middleman-core/lib/middleman-core/renderers/erb.rb
@@ -13,7 +13,7 @@ module Middleman
         def precompiled_preamble(locals)
           original = super
           "__in_erb_template = true\n" << original
-          # .rpartition("\n").first << "#{@outvar} = _buf = ActiveSupport::SafeBuffer.new\n"
+          # .rpartition("\n").first << "#{@outvar} = _buf = ::ActiveSupport::SafeBuffer.new\n"
         end
       end
     end
diff --git a/middleman-core/lib/middleman-core/renderers/redcarpet.rb b/middleman-core/lib/middleman-core/renderers/redcarpet.rb
index f08ddf5c..81c7af90 100644
--- a/middleman-core/lib/middleman-core/renderers/redcarpet.rb
+++ b/middleman-core/lib/middleman-core/renderers/redcarpet.rb
@@ -1,5 +1,4 @@
 require 'redcarpet'
-require 'active_support/core_ext/module/attribute_accessors'
 
 module Middleman
   module Renderers
diff --git a/middleman-core/lib/middleman-core/sitemap/store.rb b/middleman-core/lib/middleman-core/sitemap/store.rb
index 5c9acb6d..3170ebd0 100644
--- a/middleman-core/lib/middleman-core/sitemap/store.rb
+++ b/middleman-core/lib/middleman-core/sitemap/store.rb
@@ -1,5 +1,4 @@
 # Used for merging results of metadata callbacks
-require 'active_support/core_ext/hash/deep_merge'
 require 'monitor'
 require 'hamster'
 require 'middleman-core/extensions'
diff --git a/middleman-core/lib/middleman-core/template_renderer.rb b/middleman-core/lib/middleman-core/template_renderer.rb
index 03492838..9c29ca67 100644
--- a/middleman-core/lib/middleman-core/template_renderer.rb
+++ b/middleman-core/lib/middleman-core/template_renderer.rb
@@ -1,6 +1,5 @@
 require 'tilt'
 require 'hamster'
-require 'active_support/core_ext/string/output_safety'
 require 'middleman-core/contracts'
 require 'middleman-core/template_context'
 require 'middleman-core/file_renderer'
diff --git a/middleman-core/lib/middleman-core/util.rb b/middleman-core/lib/middleman-core/util.rb
index 9247e0e7..6f5f790f 100644
--- a/middleman-core/lib/middleman-core/util.rb
+++ b/middleman-core/lib/middleman-core/util.rb
@@ -1,6 +1,3 @@
-# For instrumenting
-require 'active_support/notifications'
-
 require 'middleman-core/application'
 require 'middleman-core/sources'
 require 'middleman-core/sitemap/resource'
diff --git a/middleman-core/lib/middleman-core/util/uri_templates.rb b/middleman-core/lib/middleman-core/util/uri_templates.rb
index 9fe1d772..1d8f04d6 100644
--- a/middleman-core/lib/middleman-core/util/uri_templates.rb
+++ b/middleman-core/lib/middleman-core/util/uri_templates.rb
@@ -1,8 +1,6 @@
 # For URI templating
 require 'addressable/uri'
 require 'addressable/template'
-require 'active_support/inflector'
-require 'active_support/inflector/transliterate'
 
 module Middleman
   module Util
diff --git a/middleman-core/spec/spec_helper.rb b/middleman-core/spec/spec_helper.rb
index 563337a1..d808b2a4 100644
--- a/middleman-core/spec/spec_helper.rb
+++ b/middleman-core/spec/spec_helper.rb
@@ -1,3 +1,6 @@
+require 'backports/latest'
+require 'active_support/all'
+
 require 'simplecov'
 SimpleCov.root(File.expand_path(File.dirname(__FILE__) + '/..'))
 SimpleCov.start