diff --git a/middleman-core/features/encoding_option.feature b/middleman-core/features/encoding_option.feature
new file mode 100644
index 00000000..b2aeed6b
--- /dev/null
+++ b/middleman-core/features/encoding_option.feature
@@ -0,0 +1,23 @@
+# encoding: iso-8859-1
+Feature: encoding option
+
+  Scenario: No encoding set
+    Given a fixture app "clean-app"
+    Given the Server is running at "clean-app"
+
+    When I go to "/index.html"
+    Then the "Content-Type" header should contain "text/html"
+    Then the "Content-Type" header should contain "charset=utf-8"
+
+  Scenario: Custom encoding set
+    Given a fixture app "i-8859-1-app"
+    And a file named "config.rb" with:
+      """
+      set :encoding, "ISO-8859-1"
+      """
+    Given the Server is running at "i-8859-1-app"
+
+    When I go to "/index.html"
+    Then the "Content-Type" header should contain "text/html"
+    Then the "Content-Type" header should contain "charset=iso-8859-1"
+    Then I should see "äöü"
diff --git a/middleman-core/fixtures/i-8859-1-app/config.rb b/middleman-core/fixtures/i-8859-1-app/config.rb
new file mode 100644
index 00000000..3252ee63
--- /dev/null
+++ b/middleman-core/fixtures/i-8859-1-app/config.rb
@@ -0,0 +1 @@
+set :encoding, "ISO-8859-1"
diff --git a/middleman-core/fixtures/i-8859-1-app/source/index.html.erb b/middleman-core/fixtures/i-8859-1-app/source/index.html.erb
new file mode 100644
index 00000000..3c015801
--- /dev/null
+++ b/middleman-core/fixtures/i-8859-1-app/source/index.html.erb
@@ -0,0 +1 @@
+äöü
diff --git a/middleman-core/lib/middleman-core/application.rb b/middleman-core/lib/middleman-core/application.rb
index ff2d4e4f..5818548b 100644
--- a/middleman-core/lib/middleman-core/application.rb
+++ b/middleman-core/lib/middleman-core/application.rb
@@ -253,11 +253,6 @@ module Middleman
       # Initialize the Sitemap
       @sitemap = ::Middleman::Sitemap::Store.new(self)
 
-      if Object.const_defined?(:Encoding)
-        Encoding.default_internal = config[:encoding]
-        Encoding.default_external = config[:encoding]
-      end
-
       ::Middleman::Extension.clear_after_extension_callbacks
 
       after_configuration_eval(&method(:prune_tilt_templates))
@@ -276,6 +271,10 @@ module Middleman
       # Eval config.
       evaluate_configuration!
 
+      if Object.const_defined?(:Encoding)
+        Encoding.default_external = config[:encoding]
+      end
+
       # Run any `configure` blocks for the current environment.
       execute_callbacks([:configure, config[:environment]])
 
diff --git a/middleman-core/lib/middleman-core/step_definitions/server_steps.rb b/middleman-core/lib/middleman-core/step_definitions/server_steps.rb
index 9ff79474..7defbbc0 100644
--- a/middleman-core/lib/middleman-core/step_definitions/server_steps.rb
+++ b/middleman-core/lib/middleman-core/step_definitions/server_steps.rb
@@ -75,6 +75,10 @@ Then /^the content type should be "([^\"]*)"$/ do |expected|
   expect(page.response_headers['Content-Type']).to start_with expected
 end
 
+Then /^the "([^\"]*)" header should contain "([^\"]*)"$/ do |header, expected|
+  expect(page.response_headers[header]).to include expected
+end
+
 Then /^I should see "([^\"]*)"$/ do |expected|
   expect(page.body).to include expected
 end