diff --git a/config/software/ruby.rb b/config/software/ruby.rb
index 70bf0a921..fdbe34fb3 100644
--- a/config/software/ruby.rb
+++ b/config/software/ruby.rb
@@ -311,15 +311,17 @@
   end
 
   if windows?
-    puts "START - searching for openssl.so instances"
-    puts "opscode dir:"
-    Dir["#{install_dir}/**/openssl.so"]
-    puts "install dir:"
-    Dir["#{project_dir}/**/openssl.so"]
-    puts "Msys path:"
-    msys_path = ENV["MSYS2_INSTALL_DIR"] ? "#{ENV["MSYS2_INSTALL_DIR"]}" : "#{ENV["OMNIBUS_TOOLCHAIN_INSTALL_DIR"]}/embedded/bin"
-    Dir["#{msys_path}/**/openssl.so"]
-    puts "END - searching for openssl.so instances"
+    def find_files
+      puts "START - searching for openssl.so instances"
+      puts "opscode dir:"
+      Dir["#{install_dir}/**/openssl.so"]
+      puts "install dir:"
+      Dir["#{project_dir}/**/openssl.so"]
+      puts "Msys path:"
+      msys_path = ENV["MSYS2_INSTALL_DIR"] ? "#{ENV["MSYS2_INSTALL_DIR"]}" : "#{ENV["OMNIBUS_TOOLCHAIN_INSTALL_DIR"]}/embedded/bin"
+      Dir["#{msys_path}/**/openssl.so"]
+      puts "END - searching for openssl.so instances"
+    end
     # Needed now that we switched to msys2 and have not figured out how to tell
     # it how to statically link yet
     %w{ erb gem irb rdoc ri bundle }.each do |cmd|
@@ -329,6 +331,7 @@
     # Ruby seems to mark rake.bat as read-only.
     # Mark it as writable so that we can install other version of rake without
     # running into permission errors.
+    command find_files
     command "attrib -r #{install_dir}/embedded/bin/rake.bat"
 
   end