diff --git a/lib/ditty/components/ditty.rb b/lib/ditty/components/ditty.rb
index c19f86d..f78d4b9 100644
--- a/lib/ditty/components/ditty.rb
+++ b/lib/ditty/components/ditty.rb
@@ -9,6 +9,9 @@ def self.load
       controllers = File.expand_path('../controllers', __dir__)
       Dir.glob("#{controllers}/*.rb").sort.each { |f| require f }
 
+      services = File.expand_path('../services', __dir__)
+      Dir.glob("#{services}/*.rb").sort.each { |f| require f }
+
       require 'ditty/models/user'
       require 'ditty/models/role'
       require 'ditty/models/identity'
@@ -19,6 +22,8 @@ def self.load
     def self.configure(_container)
       require 'ditty/db' unless defined? ::DB
       require 'ditty/listener'
+
+      self.load
     end
 
     def self.migrations
diff --git a/lib/ditty/controllers/application_controller.rb b/lib/ditty/controllers/application_controller.rb
index e7aa5c6..88d4a42 100644
--- a/lib/ditty/controllers/application_controller.rb
+++ b/lib/ditty/controllers/application_controller.rb
@@ -11,6 +11,7 @@
 require 'ditty/helpers/pundit'
 require 'ditty/helpers/authentication'
 require 'ditty/services/logger'
+require 'ditty/middleware/telemetry'
 require 'active_support'
 require 'active_support/inflector'
 require 'rack/contrib'
@@ -36,6 +37,7 @@ class ApplicationController < Sinatra::Base
 
     register Sinatra::Flash, Sinatra::RespondWith
 
+    use Middleware::Telemetry
     use Rack::JSONBodyParser
     use Rack::MethodOverride
     use Rack::NestedParams
@@ -65,6 +67,15 @@ def config(name, default = '')
       end
     end
 
+    # Fine for certain things, but using middleware might be a better idea
+    before do
+      broadcast(:before_route, target: self)
+    end
+
+    after do
+      broadcast(:after_route, target: self)
+    end
+
     def view_folders
       folders = ['./views']
       folders << settings.view_folder if settings.view_folder
@@ -98,6 +109,7 @@ def find_template(views, name, engine, &block)
     end
 
     not_found do
+      broadcast(:application_error, env['sinatra.error'], error_code: 404, target: self)
       respond_to do |format|
         status 404
         format.html do
@@ -114,7 +126,7 @@ def find_template(views, name, engine, &block)
     end
 
     error Helpers::NotAuthenticated, ::Pundit::NotAuthorizedError do
-      # TODO: Check if this is logged / tracked
+      broadcast(:application_error, env['sinatra.error'], error_code: 403, target: self)
       if authenticated?
         respond_to do |format|
           status 403
@@ -141,6 +153,7 @@ def find_template(views, name, engine, &block)
     end
 
     error ::Sinatra::Param::InvalidParameterError do
+      broadcast(:application_error, env['sinatra.error'], error_code: 400, target: self)
       respond_to do |format|
         status 400
         format.html do
@@ -155,6 +168,7 @@ def find_template(views, name, engine, &block)
     end
 
     error ::Sequel::NoMatchingRow do
+      broadcast(:application_error, env['sinatra.error'], error_code: 404, target: self)
       respond_to do |format|
         status 404
         format.html do
@@ -171,6 +185,7 @@ def find_template(views, name, engine, &block)
     end
 
     error ::Sequel::ValidationFailed do
+      broadcast(:application_error, env['sinatra.error'], error_code: 400, target: self)
       respond_to do |format|
         entity = env['sinatra.error'].model
         errors = env['sinatra.error'].errors
@@ -187,7 +202,7 @@ def find_template(views, name, engine, &block)
 
     error ::Sequel::ForeignKeyConstraintViolation do
       error = env['sinatra.error']
-      broadcast(:application_error, error)
+      broadcast(:application_error, error, error_code: 400, target: self)
       logger.error error
       respond_to do |format|
         status 400
@@ -203,7 +218,7 @@ def find_template(views, name, engine, &block)
     error ::Ditty::TemplateNotFoundError do
       # TODO: Display a better error message
       error = env['sinatra.error']
-      broadcast(:application_error, error)
+      broadcast(:application_error, error, error_code: 500, target: self)
       logger.error error
       respond_to do |format|
         status 500
@@ -215,7 +230,7 @@ def find_template(views, name, engine, &block)
 
     error do
       error = env['sinatra.error']
-      broadcast(:application_error, error)
+      broadcast(:application_error, error, error_code: 500, target: self)
       logger.error error
       respond_to do |format|
         status 500
diff --git a/lib/ditty/middleware/telemetry.rb b/lib/ditty/middleware/telemetry.rb
new file mode 100644
index 0000000..53206c4
--- /dev/null
+++ b/lib/ditty/middleware/telemetry.rb
@@ -0,0 +1,46 @@
+# frozen_string_literal: true
+
+require 'ditty/services/open_telemetry'
+
+module Ditty
+  module Middleware
+    class Telemetry
+      attr_reader :env, :telemetry
+
+      def initialize(app, telemetry = nil)
+        @app = app
+        @telemetry = telemetry || Services::OpenTelemetry.new
+      end
+
+      def call(env)
+        @env = env
+        request = Rack::Request.new(env)
+        attribs = {
+          ::OpenTelemetry::SemanticConventions::Trace::HTTP_URL => request.url,
+          ::OpenTelemetry::SemanticConventions::Trace::HTTP_METHOD => request.request_method,
+        }
+
+        telemetry.instrumented("#{request.request_method} #{request.path}", attribs) do |span|
+          # Not sure if we should try and catch exceptions?
+          result = @app.call(env)
+          span.add_attributes(
+            ::OpenTelemetry::SemanticConventions::Trace::HTTP_STATUS_CODE => result[0]
+          )
+          result
+        end
+      end
+
+      class << self
+        def method_missing(method, *args, &block)
+          instance.send(method, *args, &block)
+        end
+
+        def respond_to_missing?(method, _include_private)
+          return true if instance.respond_to?(method)
+
+          super
+        end
+      end
+    end
+  end
+end
diff --git a/lib/ditty/services/logger.rb b/lib/ditty/services/logger.rb
index 6766ae3..b0e90ea 100644
--- a/lib/ditty/services/logger.rb
+++ b/lib/ditty/services/logger.rb
@@ -30,7 +30,7 @@ def initialize
         end
       end
 
-      # TODO: REfac this so that you can log something like ES to a separate logger
+      # TODO: Refac this so that you can log something like ES to a separate logger
 
       def method_missing(method, *args, &block)
         loggers.each { |logger| logger.send(method, *args, &block) }
diff --git a/lib/ditty/services/open_telemetry.rb b/lib/ditty/services/open_telemetry.rb
new file mode 100644
index 0000000..000256b
--- /dev/null
+++ b/lib/ditty/services/open_telemetry.rb
@@ -0,0 +1,54 @@
+# frozen_string_literal: true
+
+module Ditty
+  module Services
+    class OpenTelemetry
+      def tracer
+        # ::OpenTelemetry::Instrumentation::Sinatra::Instrumentation.instance.tracer
+        @tracer ||= ::OpenTelemetry.tracer_provider.tracer('Ditty', ::Ditty::VERSION)
+      end
+
+      def instrumented?
+        (ENV['DITTY_TELEMETRY_ENABLED'] || 0).to_i == 1
+      end
+
+      def instrumented(span_name, attribs = {})
+        return yield unless instrumented?
+
+        tracer.in_span(span_name, attributes: base_attributes.merge(attribs)) do |span|
+          yield(span)
+        end
+      end
+
+      def application_error(error, opts = {})
+        error ||= env['sinatra.error']
+        return unless error.is_a? StandardError
+        return unless @request_span
+
+        request = opts[:target].request
+        @request_span&.record_exception(
+          error,
+          attributes: base_attributes.merge(
+            ::OpenTelemetry::SemanticConventions::Trace::HTTP_URL => request.url,
+            ::OpenTelemetry::SemanticConventions::Trace::HTTP_METHOD => request.request_method,
+            ::OpenTelemetry::SemanticConventions::Trace::HTTP_STATUS_CODE => opts[:error_code] || 500
+          )
+        )
+        if (opts[:error_code] || 500) >= 500
+          @request_span&.status = ::OpenTelemetry::Trace::Status.error("Application Error: #{error.class}")
+        end
+        @request_span&.finish
+      end
+
+      private
+
+        def base_attributes
+          {
+            'ditty.version' => ::Ditty::VERSION,
+          }
+        end
+    end
+  end
+end
+
+Wisper.subscribe(::Ditty::Services::OpenTelemetry.new, on: %i[application_error]) unless ENV['RACK_ENV'] == 'test'