Sorry -- I'm using smtp.office365.com, port 587 as the SMTP server .. I think of that as Outlook.

I'm generating a report by sending a bunch of query results to Template::Toolkit process, then I'm sending the result. I just did a test run, and the output file (a web page) was 835K, so not huge. This is the code that sends the message, using ymd as the date and output as the output from the TT2 process:

      my $message = Email::Simple::Markdown->create(
        header => [
          Subject => "Sage IC Issues to be fixed / $ymd",
          To      => $list,
          Bcc     => 'talexb@foobar.com',
          From    => 'noreply@foobar.com'
        ],  
        body => $output
      );  

      defined $message or die "Could not create message!";

      try {
        sendmail(
          $message,
          {   
            from      => 'noreply@foobar.com',
            transport => Email::Sender::Transport::SMTP->new(
              {   
                host          => $EMail::Host,
                port          => $EMail::Port,
                sasl_username => $EMail::User,
                sasl_password => $EMail::Password,
                ssl           => 'starttls',
              }   
            )   
          }   
        );  
      }   
      catch {
        warn "sending failed: $_";
      };
[download]

The complete error listing is here:

sending failed: error at during DATA: [Net::SMTP::_SSL] Connection clo
+sed

Trace begun at /usr/local/share/perl/5.34.0/Email/Sender/Transport/SMT
+P.pm line 259
Email::Sender::Transport::SMTP::_throw('Email::Sender::Transport::SMTP
+=HASH(0x5591af605fd8)', 'error at during DATA', 'Net::SMTP::_SSL=GLOB
+(0x5591b02e7890)') called at /usr/local/share/perl/5.34.0/Email/Sende
+r/Transport/SMTP.pm line 270
Email::Sender::Transport::SMTP::__ANON__('error at during DATA') calle
+d at /usr/local/share/perl/5.34.0/Email/Sender/Transport/SMTP.pm line
+ 324
Email::Sender::Transport::SMTP::send_email('Email::Sender::Transport::
+SMTP=HASH(0x5591af605fd8)', 'Email::Abstract=ARRAY(0x5591afd2b280)', 
+'HASH(0x5591afdc3f30)') called at /usr/local/share/perl/5.34.0/Email/
+Sender/Role/CommonSending.pm line 45
Email::Sender::Role::CommonSending::try {...}  at /usr/local/share/per
+l/5.34.0/Try/Tiny.pm line 102
eval {...} at /usr/local/share/perl/5.34.0/Try/Tiny.pm line 93
Try::Tiny::try('CODE(0x5591b02de808)', 'Try::Tiny::Catch=REF(0x5591afd
+cfb90)') called at /usr/local/share/perl/5.34.0/Email/Sender/Role/Com
+monSending.pm line 58
Email::Sender::Role::CommonSending::send('Email::Sender::Transport::SM
+TP=HASH(0x5591af605fd8)', 'Email::Abstract=ARRAY(0x5591afd2b280)', 'H
+ASH(0x5591b02de418)') called at /usr/local/share/perl/5.34.0/Email/Se
+nder/Simple.pm line 119
Email::Sender::Simple::send_email('Email::Sender::Simple', 'Email::Abs
+tract=ARRAY(0x5591afd2b280)', 'HASH(0x5591afdc3c90)') called at /usr/
+local/share/perl/5.34.0/Email/Sender/Role/CommonSending.pm line 45
Email::Sender::Role::CommonSending::try {...}  at /usr/local/share/per
+l/5.34.0/Try/Tiny.pm line 102
eval {...} at /usr/local/share/perl/5.34.0/Try/Tiny.pm line 93
Try::Tiny::try('CODE(0x5591afdc3fd8)', 'Try::Tiny::Catch=REF(0x5591afc
+c9ea8)') called at /usr/local/share/perl/5.34.0/Email/Sender/Role/Com
+monSending.pm line 58
Email::Sender::Role::CommonSending::send('Email::Sender::Simple', 'Ema
+il::Simple::Markdown=HASH(0x5591afcc2fc0)', 'HASH(0x5591af605f30)') c
+alled at /usr/local/share/perl/5.34.0/Sub/Exporter/Util.pm line 57
Sub::Exporter::Util::__ANON__('Email::Simple::Markdown=HASH(0x5591afcc
+2fc0)', 'HASH(0x5591af605f30)') called at sage_issues.pl line 175
main::try {...}  at /usr/local/share/perl/5.34.0/Try/Tiny.pm line 102
eval {...} at /usr/local/share/perl/5.34.0/Try/Tiny.pm line 93
Try::Tiny::try('CODE(0x5591afcb89c0)', 'Try::Tiny::Catch=REF(0x5591ad4
+ae5a0)') called at script.pl line 42
[download]