This works for me, but I also don't have issues with my openssl or IO::Socket::SSL. I'd look there first. 
    my $config = Config::Tiny->new();
    $config = Config::Tiny->read($config_file);

    my $transport = Email::Sender::Transport::SMTP::TLS->new(
        host          => $config->{email}->{smtp_host},
        port          => 587,     # defaults to TLS if not set
        username => 'bgates@microsoft.com',
        password => '66Fc1eb207d4380',
        helo     => 'HELO',
    );

    my $message = Email::Simple->create(
        header => [
            From         => 'bgates@microsoft.com',
            To              => $to,
            Subject     => $subject,
        ],
        body => $content,
    );

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In reply to Re: sending email with starttls not working by perlfan
in thread sending email with starttls not working by jfwell

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