diff --git a/bridgetown-core/lib/bridgetown-core/commands/build.rb b/bridgetown-core/lib/bridgetown-core/commands/build.rb
index 0b5194ca0..1dc6e0adc 100644
--- a/bridgetown-core/lib/bridgetown-core/commands/build.rb
+++ b/bridgetown-core/lib/bridgetown-core/commands/build.rb
@@ -50,11 +50,7 @@ def build
           if Bridgetown::Utils.frontend_bundler_type(config_options[:root_dir]) == :esbuild
             Bridgetown::Utils.update_esbuild_autogenerated_config config_options
           end
-          require "rake"
-          Rake.with_application do |rake|
-            rake.load_rakefile
-            rake["frontend:watcher"].invoke(true)
-          end
+          invoke_frontend_watcher_from_rake
         end
 
         @site = Bridgetown::Site.new(config_options)
@@ -125,6 +121,21 @@ def display_folder_paths(config_options)
         plugins_dir = File.expand_path(config_options["plugins_dir"])
         Bridgetown.logger.info "Custom Plugins:", plugins_dir if Dir.exist?(plugins_dir)
       end
+
+      def invoke_frontend_watcher_from_rake
+        require "rake"
+        Rake.with_application do |rake|
+          begin
+            rake.raw_load_rakefile
+          rescue StandardError => e
+            unless e.message.include?("No Rakefile found")
+              Bridgetown.logger.error "Error Running Rake:", "#{e.message} (#{e.class})"
+              e.backtrace[0..1].each { |backtrace_line| Bridgetown.logger.info backtrace_line }
+            end
+          end
+          rake["frontend:watcher"].invoke(true) if rake.tasks.any? { _1.name == "frontend:watcher" }
+        end
+      end
     end
   end
 end
diff --git a/bridgetown-core/lib/bridgetown-core/commands/start.rb b/bridgetown-core/lib/bridgetown-core/commands/start.rb
index 0dca6c21c..e7c47f73f 100644
--- a/bridgetown-core/lib/bridgetown-core/commands/start.rb
+++ b/bridgetown-core/lib/bridgetown-core/commands/start.rb
@@ -84,7 +84,7 @@ def start
         Bridgetown::Server.new({
           Host: bt_options.bind,
           Port: port,
-          config: "config.ru",
+          config: rack_config_file,
         }).tap do |server|
           if server.serveable?
             pid_tracker.create_pid_dir
@@ -117,6 +117,14 @@ def start
           end
         end
       end
+
+      protected
+
+      def rack_config_file
+        File.exist?("config.ru") ?
+          "config.ru" :
+          File.expand_path("../rack/default_config.ru", __dir__)
+      end
     end
   end
 end
diff --git a/bridgetown-core/lib/bridgetown-core/configuration.rb b/bridgetown-core/lib/bridgetown-core/configuration.rb
index dec848e8c..68bbd2ca7 100644
--- a/bridgetown-core/lib/bridgetown-core/configuration.rb
+++ b/bridgetown-core/lib/bridgetown-core/configuration.rb
@@ -129,7 +129,10 @@ def from(user_config, starting_defaults = DEFAULTS)
 
     def run_initializers!(context:) # rubocop:todo Metrics/AbcSize, Metrics/CyclomaticComplexity
       initializers_file = File.join(root_dir, "config", "initializers.rb")
-      return unless File.file?(initializers_file)
+      unless File.file?(initializers_file)
+        setup_load_paths! appending: true
+        return
+      end
 
       load initializers_file
 
@@ -287,13 +290,13 @@ def merge_environment_specific_options!
     end
 
     def setup_load_paths!(appending: false) # rubocop:todo Metrics
-      unless appending
-        self[:root_dir] = File.expand_path(self[:root_dir])
-        self[:source] = File.expand_path(self[:source], self[:root_dir])
-        self[:destination] = File.expand_path(self[:destination], self[:root_dir])
+      self[:root_dir] = File.expand_path(self[:root_dir])
+      self[:source] = File.expand_path(self[:source], self[:root_dir])
+      self[:destination] = File.expand_path(self[:destination], self[:root_dir])
 
+      unless appending
         autoload_paths.unshift({
-          path: self[:plugins_dir],
+          path: File.expand_path(self[:plugins_dir], self[:root_dir]),
           eager: true,
         })
         autoload_paths.unshift({
diff --git a/bridgetown-core/lib/bridgetown-core/rack/default_config.ru b/bridgetown-core/lib/bridgetown-core/rack/default_config.ru
new file mode 100644
index 000000000..7b959c7f4
--- /dev/null
+++ b/bridgetown-core/lib/bridgetown-core/rack/default_config.ru
@@ -0,0 +1,14 @@
+# frozen_string_literal: true
+
+require "bridgetown-core/rack/boot"
+
+Bridgetown::Rack.boot
+
+unless defined?(RodaApp)
+  class RodaApp < Roda
+    plugin :bridgetown_server
+    route(&:bridgetown)
+  end
+end
+
+run RodaApp.freeze.app
diff --git a/bridgetown-foundation/lib/bridgetown/foundation/packages/pid_tracker.rb b/bridgetown-foundation/lib/bridgetown/foundation/packages/pid_tracker.rb
index 39994d090..a4c569262 100644
--- a/bridgetown-foundation/lib/bridgetown/foundation/packages/pid_tracker.rb
+++ b/bridgetown-foundation/lib/bridgetown/foundation/packages/pid_tracker.rb
@@ -13,10 +13,13 @@ def add_pid(pid, file:)
 
       def read_pidfile(file)
         File.readlines pidfile_for(file), chomp: true
+      rescue SystemCallError
+        []
       end
 
       def remove_pidfile(file)
         File.delete pidfile_for(file)
+      rescue SystemCallError # rubocop:disable Lint/SuppressedException
       end
 
       private
diff --git a/bridgetown-website/config.ru b/bridgetown-website/config.ru
deleted file mode 100644
index 80ee3495e..000000000
--- a/bridgetown-website/config.ru
+++ /dev/null
@@ -1,7 +0,0 @@
-# This file is used by Rack-based servers during the Bridgetown boot process.
-
-require "bridgetown-core/rack/boot"
-
-Bridgetown::Rack.boot
-
-run RodaApp.freeze.app # see server/roda_app.rb
diff --git a/bridgetown-website/server/roda_app.rb b/bridgetown-website/server/roda_app.rb
index 921e63ebc..6b495ed56 100644
--- a/bridgetown-website/server/roda_app.rb
+++ b/bridgetown-website/server/roda_app.rb
@@ -7,7 +7,5 @@
 class RodaApp < Roda
   plugin :bridgetown_server
 
-  route do |r|
-    r.bridgetown
-  end
+  route(&:bridgetown)
 end