What's your requirement? That is be installed on Windows as a standalone program or that you can send email on Windows using a Perl script? You seem to be over complicating it with this bit-rotten program. So if you're looking for options; give us the constraints and look into any suggestions you get. In 2021, sending email is pretty darn easy with a number of useful and easy to use modules on CPAN.
Comment on Re: pp generated executable can't find or load libraries
My requirement is to get sendemail.exe to be installed on Windows as a standalone program with TLSv1.2 support. I know there is a million way to send emails but unfortunately the original sendEmail.exe v1.56 from 2009 is used in a legacy (old and complicated) app, and I was simply hoping to package it with TLSv1.2 support to avoid the need to update the legacy app.