diff --git a/config/software/ruby.rb b/config/software/ruby.rb
index 4a2d6f2294..99817e7564 100644
--- a/config/software/ruby.rb
+++ b/config/software/ruby.rb
@@ -357,25 +357,29 @@
   end
 
   if fips_mode?
-    puts "<<<<<<< FIPS MODE >>>>>>>"
+    puts "Validating FIPS_MODE build"
     if windows?
+      puts "Reinstalling the openssl gem for Windows since it is installed with 1.1.1t for 3.1.x rubyinstaller"
       command "#{install_dir}/embedded/bin/gem install openssl -- --with-openssl-dir=#{install_dir}/embedded", env: env.merge({"OPENSSL_FIPS" => "1"})
+
+      puts "Finding all the rubies installed and checking their fips_mode status"
       find_command = %(
         Get-ChildItem c:/opscode -name 'ruby.exe' -recurse | ForEach-Object {
-          & $_ -e "require 'openssl'; puts OpenSSL::OPENSSL_VERSION_NUMBER.to_s(16); puts OpenSSL::OPENSSL_LIBRARY_VERSION; OpenSSL.fips_mode = 1"
+          & $_ -e "require 'openssl'; puts OpenSSL::OPENSSL_VERSION_NUMBER.to_s(16); puts OpenSSL::OPENSSL_LIBRARY_VERSION; OpenSSL.fips_mode = 1; puts 'FIPS mode successfully activated for Ruby' + RUBY_VERSION"
         }
+        Write-Output "done looking at rubies"
       )
+      command find_command
     else
       find_command = %(
         find /opt -name 'ruby' | grep 'bin/ruby' | while read ruby; do
           echo "Checking $ruby"
           sum $ruby
-          $ruby -v -e "require 'openssl'; puts OpenSSL::OPENSSL_VERSION_NUMBER.to_s(16); puts OpenSSL::OPENSSL_LIBRARY_VERSION; OpenSSL.fips_mode = 1"
+          $ruby -v -e "require 'openssl'; puts OpenSSL::OPENSSL_VERSION_NUMBER.to_s(16); puts OpenSSL::OPENSSL_LIBRARY_VERSION; OpenSSL.fips_mode = 1; puts 'FIPS mode successfully activated for Ruby '+ RUBY_VERSION"
         done
         echo "done looking at rubies"
       )
       command find_command
     end
-    puts ">>>>>>> FIPS MODE <<<<<<<"
   end
 end