Use upstart script

chef/cookbooks/metasploitable/files/sinatra/Gemfile

@@ -1,6 +1,5 @@
 source 'https://rubygems.org'
-gem 'rack', '1.6.5'
-gem 'sinatra', '1.4.8'
-gem 'erubis'
+gem 'rack', '2.0.1'
+gem 'sinatra', '2.0.0rc2'
 gem 'erubis'
 gem 'activesupport'

chef/cookbooks/metasploitable/files/sinatra/README.txt

@@ -28,4 +28,4 @@ And then finally:
 
 $ ruby start.rb
 
-The server should start on port 8080.
+The server should start on port 8181.

chef/cookbooks/metasploitable/files/sinatra/server.rb

@@ -3,6 +3,7 @@
 require 'sinatra'
 require 'erubis'
 require 'active_support'
+require 'webrick'
 
 MYSECRET = 'a7aebc287bba0ee4e64f947415a94e5f'
 
@@ -10,6 +11,12 @@ set :environment, :development
 set :bind, '0.0.0.0'
 set :port, 8181
 
+# These settings are specific for Sinatra 2.0.0rc2
+set :logging, false
+set :quiet, true
+dev_null = WEBrick::Log::new("/dev/null", 7)
+set :server_settings, {:Logger => dev_null, :AccessLog => dev_null}
+
 use Rack::Session::Cookie,
   :key          => "_metasploitable",
   :path         => "/",

chef/cookbooks/metasploitable/files/sinatra/sinatra.conf

@@ -0,0 +1,5 @@
+description 'Run vulnerable Sinatra'
+author 'metasploitable3'
+
+start on runlevel [2345]
+exec "/opt/sinatra/start.sh"

chef/cookbooks/metasploitable/files/sinatra/sinatra.sh

@@ -12,7 +12,7 @@
 
 case "$1" in
  start)
-   /opt/sinatra/start.rb
+   /opt/sinatra/start.sh
    ;;
  *)
    echo "Usage: start {start}" >&2

chef/cookbooks/metasploitable/recipes/sinatra.rb

@@ -9,43 +9,30 @@
 include_recipe 'metasploitable::sinatra'
 
 apt_repository 'rvm' do
-  uri 'ppa:rael-gc/rvm'
+  uri 'ppa:brightbox/ruby-ng'
 end
 
-package 'rvm'
+package 'ruby2.3'
 
-bash 'run rvm.sh' do
-  code <<-EOH
-  source /etc/profile.d/rvm.sh
-  rvmsudo rvm install ruby-2.3.1
-  rvm --default use 2.3.1
-  gem install bundler
-  EOH
-end
+package 'bundler'
 
 directory '/opt/sinatra' do
   mode '0777'
 end
 
-['Gemfile', 'README.txt', 'check.rb', 'poc.rb', 'start.rb'].each do |fname|
+['Gemfile', 'README.txt', 'check.rb', 'poc.rb', 'start.sh', 'server.rb'].each do |fname|
   cookbook_file "/opt/sinatra/#{fname}" do
     source "sinatra/#{fname}"
     mode '0777'
   end
 end
 
-bash 'bundle install sinatra' do
-  code <<-EOH
-  cd /opt/sinatra
-  bundle install
-  EOH
-end
-
-cookbook_file '/etc/init.d/sinatra' do
-  source 'sinatra/sinatra.sh'
+cookbook_file '/etc/init/sinatra.conf' do
+  source 'sinatra/sinatra.conf'
   mode '0777'
 end
 
 service 'sinatra' do
+  supports restart: false, start: true, reload: false, status: false
   action [:enable, :start]
 end