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]

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]

What does the SMTP server complain about that causes E'S'T'SMTP to croak? That is say log for the exchange between the client & server is missing.

...
Net::SMTP::_SSL=GLOB(0x5606ff569450)>>> lass=3D'left'>1     </td>     
+  <td class=3D'left'>Covermaster 8 Roll Trans
Net::SMTP::_SSL: Net::Cmd::_syswrite_with_timeout(): unexpected EOF on
+ command channel: Connection reset by peer at /usr/local/share/perl/5
+.34.0/Email/Sender/Transport/SMTP.pm line 324.
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
...
[download]

It looks like there's a timeout .. it took ~10 minutes to fail.

Alex / talexb / Toronto

Thanks PJ. We owe you so much. Groklaw -- RIP -- 2003 to 2013.

Right .. the debug flag. I'll try that when I get back to my office. Thanks!

Alex / talexb / Toronto

Thanks PJ. We owe you so much. Groklaw -- RIP -- 2003 to 2013.