Hello bdegan2, and welcome to the Monastery!

These emails are currently being sent out successfully with Net::SMTP; I was trying to use Net::SMTP::TLS...

From the documentation, it appears that Net::SMTP::TLS is no longer needed. has another module, Net::SMTP::TLS::ButMaintained, which is 7 years more up-to-date, but that module is deprecated in favour of Net::SMTPS. But the documentation for Net::SMTPS says:

As of Version 3.10 of Net::SMTP(libnet) includes SSL/STARTTLS capabilities, so this wrapper module's significance disappareing. (sic)

And the documentation of Net::SMTP 3.10 says:

With IO::Socket::SSL installed it also provides support for implicit and explicit TLS encryption, i.e. SMTPS or SMTP+STARTTLS.

So, if you install IO::Socket::SSL and upgrade Net::SMTP to 3.10 (the latest version), you can forget about Net::SMTP::TLS.

Hope that helps,