diff --git a/.rubocop.yml b/.rubocop.yml
index 82c6d296b..efcd70e96 100644
--- a/.rubocop.yml
+++ b/.rubocop.yml
@@ -11,9 +11,6 @@ inherit_gem:
 Bridgetown/NoPutsAllowed:
   Exclude:
     - rake/*.rake
-    - bridgetown-core/lib/bridgetown-core/commands/base.rb
-    - bridgetown-core/lib/bridgetown-core/commands/plugins.rb
-    - bridgetown-core/lib/bridgetown-core/rack/roda.rb
 
 AllCops:
   TargetRubyVersion: 2.7
diff --git a/bridgetown-core/.rubocop.yml b/bridgetown-core/.rubocop.yml
index 1b02eeeac..333cc662b 100644
--- a/bridgetown-core/.rubocop.yml
+++ b/bridgetown-core/.rubocop.yml
@@ -12,11 +12,15 @@ AllCops:
     - tmp/**/*
     - test/source/**/*
     - test/resources/src/_pages/*.rb
+    - lib/bridgetown-core/commands/base.rb
+    - lib/bridgetown-core/commands/plugins.rb
+    - lib/bridgetown-core/rack/roda.rb
     - lib/site_template/TEMPLATES/**/*
     - lib/site_template/Rakefile
     - lib/site_template/config.ru
     - lib/site_template/config/**/*
     - lib/site_template/plugins/site_builder.rb
+    - lib/site_template/server/roda_app.rb
 
 Lint/ConstantDefinitionInBlock:
   Exclude:
diff --git a/bridgetown-core/lib/bridgetown-core/rack/roda.rb b/bridgetown-core/lib/bridgetown-core/rack/roda.rb
index 5e46d4875..beeccf77b 100644
--- a/bridgetown-core/lib/bridgetown-core/rack/roda.rb
+++ b/bridgetown-core/lib/bridgetown-core/rack/roda.rb
@@ -2,6 +2,13 @@
 
 require "rack/indifferent"
 
+begin
+  # If it's in the Gemfile's :bridgetown_plugins group it's already been required, but we'll try
+  # again just to be on the safe side:
+  require "bridgetown-routes"
+rescue LoadError
+end
+
 class Roda
   module RodaPlugins
     module BridgetownSSR
@@ -12,6 +19,34 @@ def self.configure(app, _opts = {}, &block)
     end
 
     register_plugin :bridgetown_ssr, BridgetownSSR
+
+    module BridgetownBoot
+      module InstanceMethods
+        # Helper shorthand for Bridgetown::Current.site
+        # @return [Bridgetown::Site]
+        def bridgetown_site
+          Bridgetown::Current.site
+        end
+      end
+
+      Roda::RodaRequest.alias_method :_previous_roda_cookies, :cookies
+
+      module RequestMethods
+        # Monkeypatch Roda/Rack's Request object so it returns a hash which allows for
+        # indifferent access
+        def cookies
+          # TODO: maybe replace with a simpler hash that offers an overloaded `[]` method
+          _previous_roda_cookies.with_indifferent_access
+        end
+
+        # Starts up the Bridgetown routing system
+        def bridgetown
+          Bridgetown::Rack::Routes.start!(scope)
+        end
+      end
+    end
+
+    register_plugin :bridgetown_boot, BridgetownBoot
   end
 end
 
@@ -24,6 +59,7 @@ class Roda < ::Roda
       plugin :json_parser
       plugin :cookies
       plugin :streaming
+      plugin :bridgetown_boot
       plugin :public, root: Bridgetown::Current.preloaded_configuration.destination
       plugin :not_found do
         output_folder = Bridgetown::Current.preloaded_configuration.destination
@@ -56,12 +92,6 @@ class Roda < ::Roda
           "<p>ERROR: cannot find <code>index.html</code> in the output folder.</p>"
         end
       end
-
-      # Helper shorthand for Bridgetown::Current.site
-      # @return [Bridgetown::Site]
-      def bridgetown_site
-        Bridgetown::Current.site
-      end
     end
   end
 end
diff --git a/bridgetown-core/lib/site_template/server/roda_app.rb b/bridgetown-core/lib/site_template/server/roda_app.rb
index bfd452e85..eaebb69ae 100644
--- a/bridgetown-core/lib/site_template/server/roda_app.rb
+++ b/bridgetown-core/lib/site_template/server/roda_app.rb
@@ -4,21 +4,18 @@
 #
 # Learn more at: http://roda.jeremyevans.net
 
-# Uncomment to use file-based dynamic routing in your project (make sure you
-# uncomment the gem dependency in your Gemfile as well):
-# require "bridgetown-routes"
-
 class RodaApp < Bridgetown::Rack::Roda
   # Add additional Roda configuration here if needed
 
   # Uncomment to use Bridgetown SSR:
   # plugin :bridgetown_ssr
 
-  # And optionally file-based routing:
+  # Uncomment to use file-based dynamic routing in your project (make sure you
+  # uncomment the gem dependency in your `Gemfile` as well):
   # plugin :bridgetown_routes
 
   route do |r|
     # Load Roda routes in server/routes (and src/_routes via `bridgetown-routes`)
-    Bridgetown::Rack::Routes.start! self
+    r.bridgetown
   end
 end
diff --git a/bridgetown-core/test/ssr/server/roda_app.rb b/bridgetown-core/test/ssr/server/roda_app.rb
index 7c7570f66..ecdff6a3c 100644
--- a/bridgetown-core/test/ssr/server/roda_app.rb
+++ b/bridgetown-core/test/ssr/server/roda_app.rb
@@ -6,7 +6,5 @@ class RodaApp < Bridgetown::Rack::Roda
     site.data.iterations += 1
   end
 
-  route do |_r|
-    Bridgetown::Rack::Routes.start! self
-  end
+  route(&:bridgetown)
 end
diff --git a/bridgetown-core/test/ssr/server/routes/cookies.rb b/bridgetown-core/test/ssr/server/routes/cookies.rb
new file mode 100644
index 000000000..9da5d964c
--- /dev/null
+++ b/bridgetown-core/test/ssr/server/routes/cookies.rb
@@ -0,0 +1,20 @@
+# frozen_string_literal: true
+
+class Routes::Cookies < Bridgetown::Rack::Routes
+  route do |r|
+    # route: GET /cookies
+    r.get "cookies" do
+      { value: r.cookies[:test_key] }
+    end
+
+    # route: POST /cookies
+    r.post "cookies" do
+      response.set_cookie :test_key, {
+        value: r.params[:value],
+        httponly: true,
+      }
+
+      { value: r.cookies[:test_key] }
+    end
+  end
+end
diff --git a/bridgetown-core/test/ssr/server/routes/ooh_json.rb b/bridgetown-core/test/ssr/server/routes/ooh_json.rb
new file mode 100644
index 000000000..85ecf5446
--- /dev/null
+++ b/bridgetown-core/test/ssr/server/routes/ooh_json.rb
@@ -0,0 +1,12 @@
+# frozen_string_literal: true
+
+class Routes::OohJson < Bridgetown::Rack::Routes
+  route do |r|
+    # route: POST /cookies
+    r.post "ooh_json" do
+      next { keep_on: "running" } unless r.params[:tell_me] == "what you're chasin'"
+
+      { because_the_night: "will never give you what you want" }
+    end
+  end
+end
diff --git a/bridgetown-core/test/test_ssr.rb b/bridgetown-core/test/test_ssr.rb
index 502eff9f5..e00091158 100644
--- a/bridgetown-core/test/test_ssr.rb
+++ b/bridgetown-core/test/test_ssr.rb
@@ -9,6 +9,10 @@ def app
     @@ssr_app ||= Rack::Builder.parse_file(File.expand_path("ssr/config.ru", __dir__)).first # rubocop:disable Style/ClassVars
   end
 
+  def site
+    app.opts[:bridgetown_site]
+  end
+
   context "Roda-powered Bridgetown server" do
     setup do
       Bridgetown::Current.site = nil
@@ -32,11 +36,22 @@ def app
     end
 
     should "preserve site data between live reloads" do
-      app # ensure it's been run
-      site = @@ssr_app.opts[:bridgetown_site]
       assert_equal 1, site.data.iterations
       site.reset(soft: true)
       assert_equal 2, site.data.iterations
     end
+
+    should "support indifferent cookies" do
+      post "/cookies", value: "Gookie!"
+      get "/cookies"
+      assert last_response.ok?
+      assert_equal({ value: "Gookie!" }.to_json, last_response.body)
+    end
+
+    should "support incoming JSON payloads" do
+      post "/ooh_json", { tell_me: "what you're chasin'" }
+      assert last_response.ok?
+      assert_equal({ because_the_night: "will never give you what you want" }.to_json, last_response.body)
+    end
   end
 end
diff --git a/bridgetown-routes/lib/bridgetown-routes.rb b/bridgetown-routes/lib/bridgetown-routes.rb
index 87ff0e6c6..fb23397d1 100644
--- a/bridgetown-routes/lib/bridgetown-routes.rb
+++ b/bridgetown-routes/lib/bridgetown-routes.rb
@@ -16,6 +16,7 @@ module Routes
 
     # rubocop:disable Bridgetown/NoPutsAllowed
     def self.print_roda_routes
+      # TODO: this needs to be fully documented, currently no info on how to generate .routes.json
       routes = begin
         JSON.parse(File.read("#{Dir.pwd}/.routes.json"))
       rescue StandardError
diff --git a/bridgetown-website/server/roda_app.rb b/bridgetown-website/server/roda_app.rb
index 619d1f7e7..8efa8a48f 100644
--- a/bridgetown-website/server/roda_app.rb
+++ b/bridgetown-website/server/roda_app.rb
@@ -7,9 +7,7 @@
 class RodaApp < Bridgetown::Rack::Roda
   plugin :bridgetown_ssr
 
-  route do
-    # Load all the files in server/routes
-    # see hello.rb.sample
-    Bridgetown::Rack::Routes.start! self
+  route do |r|
+    r.bridgetown
   end
 end
diff --git a/bridgetown-website/src/_docs/routes.md b/bridgetown-website/src/_docs/routes.md
index da0d8699f..dbe732c4e 100644
--- a/bridgetown-website/src/_docs/routes.md
+++ b/bridgetown-website/src/_docs/routes.md
@@ -157,12 +157,6 @@ To opt-into the `bridgetown-routes` gem, make sure it's enabled in your `Gemfile
 gem "bridgetown-routes", group: :bridgetown_plugins
 ```
 
-and required at the top of your `server/roda_app.rb` file:
-
-```ruby
-require "bridgetown-routes"
-```
-
 and added in as a Roda plugin below the SSR plugin:
 
 ```ruby