diff --git a/spec/acceptance/chain_key_spec.rb b/spec/acceptance/chain_key_spec.rb
index 4894bc6..4c7095b 100644
--- a/spec/acceptance/chain_key_spec.rb
+++ b/spec/acceptance/chain_key_spec.rb
@@ -1,153 +1,167 @@
 # frozen_string_literal: true
 
 require 'spec_helper_acceptance'
 
 describe 'managing intermediate certificates' do
   # rubocop:disable RSpec/InstanceVariable : Instance variables are inherited and thus cannot be contained within lets
   describe 'managing combined and seperate java chain keys' do
     include_context 'common variables'
 
+    it 'verifies keytool is setup', unless: os[:family] == 'windows' do
+      i = 0
+      loop do
+        keytool_status = run_shell('keytool')
+        break if keytool_status['exit_code'] == 0
+        if i == 10
+          exit 1
+        else
+          i += 1
+          sleep 1.minute
+        end
+      end
+    end
+
     it 'creates two private key with chain certs' do
       pp = <<-MANIFEST
         java_ks { 'combined.example.com:#{@temp_dir}chain_combined_key.ks':
           ensure       => latest,
           certificate  => "#{@temp_dir}leafchain.pem",
           private_key  => "#{@temp_dir}leafkey.pem",
           password     => 'puppet',
           path         => #{@resource_path},
         }
 
         java_ks { 'seperate.example.com:#{@temp_dir}chain_key.ks':
           ensure       => latest,
           certificate  => "#{@temp_dir}leaf.pem",
           chain        => "#{@temp_dir}chain.pem",
           private_key  => "#{@temp_dir}leafkey.pem",
           password     => 'puppet',
           path         => #{@resource_path},
         }
       MANIFEST
 
       idempotent_apply(pp)
     end
 
     expectations_combined = [
       %r{Alias name: combined\.example\.com},
       %r{Entry type: (keyEntry|PrivateKeyEntry)},
       %r{Certificate chain length: 3},
       %r{^Serial number: 5.*^Serial number: 4.*^Serial number: 3}m,
     ]
     it 'verifies the private key #combined' do
       run_shell(keytool_command("-list -v -keystore #{@temp_dir}chain_combined_key.ks -storepass puppet"), expect_failures: true) do |r|
         expectations_combined.each do |expect|
           expect(r.stdout).to match(expect)
         end
       end
     end
     expectations_seperate = [
       %r{Alias name: seperate\.example\.com},
       %r{Entry type: (keyEntry|PrivateKeyEntry)},
       %r{Certificate chain length: 3},
       %r{^Serial number: 5.*^Serial number: 4.*^Serial number: 3}m,
     ]
     it 'verifies the private key #seperate' do
       run_shell(keytool_command("-list -v -keystore #{@temp_dir}chain_key.ks -storepass puppet"), expect_failures: true) do |r|
         expectations_seperate.each do |expect|
           expect(r.stdout).to match(expect)
         end
       end
     end
 
     it 'updates the two key chains' do
       pp = <<-MANIFEST
         java_ks { 'combined.example.com:#{@temp_dir}chain_combined_key.ks':
           ensure       => latest,
           certificate  => "#{@temp_dir}leafchain2.pem",
           private_key  => "#{@temp_dir}leafkey.pem",
           password     => 'puppet',
           path         => #{@resource_path},
         }
 
         java_ks { 'seperate.example.com:#{@temp_dir}chain_key.ks':
           ensure       => latest,
           certificate  => "#{@temp_dir}leaf.pem",
           chain        => "#{@temp_dir}chain2.pem",
           private_key  => "#{@temp_dir}leafkey.pem",
           password     => 'puppet',
           path         => #{@resource_path},
         }
       MANIFEST
 
       idempotent_apply(pp)
 
       expectations_combined = [
         %r{Alias name: combined\.example\.com},
         %r{Entry type: (keyEntry|PrivateKeyEntry)},
         %r{Certificate chain length: 2},
         %r{^Serial number: 5.*^Serial number: 6}m,
       ]
       run_shell(keytool_command("-list -v -keystore #{@temp_dir}chain_combined_key.ks -storepass puppet"), expect_failures: true) do |r|
         expectations_combined.each do |expect|
           expect(r.stdout).to match(expect)
         end
       end
 
       expectations_seperate = [
         %r{Alias name: seperate\.example\.com},
         %r{Entry type: (keyEntry|PrivateKeyEntry)},
         %r{Certificate chain length: 2},
         %r{^Serial number: 5.*Serial number: 6}m,
       ]
       run_shell(keytool_command("-list -v -keystore #{@temp_dir}chain_key.ks -storepass puppet"), expect_failures: true) do |r|
         expectations_seperate.each do |expect|
           expect(r.stdout).to match(expect)
         end
       end
     end
   end
 
   describe 'managing non existent java chain keys in noop' do
     include_context 'common variables'
 
     it 'does not create a new keystore in noop' do
       pp = <<-MANIFEST
         $filenames = ["#{@temp_dir}noop_ca.pem",
                       "#{@temp_dir}noop_chain.pem",
                       "#{@temp_dir}noop_privkey.pem"]
         file { $filenames:
           ensure  => file,
           content => 'content',
         } ->
         java_ks { 'broker.example.com:#{@temp_dir}noop_chain_key.ks':
           ensure       => latest,
           certificate  => "#{@temp_dir}noop_ca.pem",
           chain        => "#{@temp_dir}noop_chain.pem",
           private_key  => "#{@temp_dir}noop_privkey.pem",
           password     => 'puppet',
           path         => #{@resource_path},
         }
       MANIFEST
 
       # in noop mode, when the dependent certificate files are not present in the system,
       # java_ks will not invoke openssl to validate their status, thus noop will succeed
       apply_manifest(pp, noop: true)
     end
 
     # verifies the dependent files are missing
     ['noop_ca.pem', 'noop_chain.pem', 'noop_privkey.pem'].each do |filename|
       describe filename do
         it "doesn't exist" do
           result = remote_file_exists?("#{@temp_dir}#{filename}")
           expect(result.exit_code).to be(1)
         end
       end
     end
 
     # verifies the keystore is not created
     describe 'noop_chain_key.ks' do
       it "doesn't exist" do
         result = remote_file_exists?("#{@temp_dir}noop_chain_key.ks")
         expect(result.exit_code).to be(1)
       end
     end
   end
 end