in reply to email fails with attachments over 8kb

It seems that Google refuses to accept your mail. Usually that is because you haven't set up your domain to their liking, and/or are spamming too much.

I found that the response you get from the Google mail servers usually points you to the cause of the problem. I don't know how to make Net::SMTP return the response message from the remote server, so I can't help you much there except to turn on debugging:

    $smtp = Net::SMTP->new('mailhost',
                           Hello => 'my.mail.domain',
                           Timeout => 30,
                           Debug   => 1,
                          );

[download]

But maybe Google already dislikes you so much that they shut down your socket without telling you anything because they see in the first 8kb of your attachment that you are up to no good.

Replies are listed 'Best First'.
Re^2: email fails with attachments over 8kb
by abrunskie (Initiate) on May 25, 2017 at 16:08 UTC
    Yes, that sort of makes sense except for the fact that a previously compiled version works perfectly. Google isn't refusing any attachments when I use that version using all the same credentials.
[reply]

      So that begs the question .. what are the differences between the version that works perfectly, and this version?

      Alex / talexb / Toronto

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

[reply]
        That's the million dollar question. I have no way of knowing because I can't decompile the executable that works. Here's some code I got off the internet yesterday that uses Net::SMTP::SSL. I get the exact same problem when I use this code. If you test it with your email specs and add an attachment in the appropriate spot I would be interested to hear your results. 
        #!/usr/bin/perl -w

use Net::SMTP::SSL;
use MIME::Base64;
use File::Spec;
use LWP::MediaTypes;

sub send_mail_with_attachments {
 my $to = shift(@_);
 my $subject = shift(@_);
 my $body = shift(@_);
 my @attachments = @_;

 my $from = 'your_email_address';
 my $password = 'your_password';

 my $smtp;

 if (not $smtp = Net::SMTP::SSL->new('your_smtp_server',
                              Port => 465,
                              Debug => 1)) {
     die "Could not connect to server\n";
 }

 # Authenticate
 $smtp->auth($from, $password)
     || die "Authentication failed!\n";

 # Create arbitrary boundary text used to seperate
 # different parts of the message
 my ($bi, $bn, @bchrs);
 my $boundry = "";
 foreach $bn (48..57,65..90,97..122) {
     $bchrs[$bi++] = chr($bn);
 }
 foreach $bn (0..20) {
     $boundry .= $bchrs[rand($bi)];
 }

 # Send the header
 $smtp->mail($from . "\n");
 my @recepients = split(/,/, $to);
 foreach my $recp (@recepients) {
     $smtp->to($recp . "\n");
 }
 $smtp->data();
 $smtp->datasend("From: " . $from . "\n");
 $smtp->datasend("To: " . $to . "\n");
 $smtp->datasend("Subject: " . $subject . "\n");
 $smtp->datasend("MIME-Version: 1.0\n");
 $smtp->datasend("Content-Type: multipart/mixed; BOUNDARY=\"$boundry\"
+\n");

 # Send the body
 $smtp->datasend("\n--$boundry\n");
 $smtp->datasend("Content-Type: text/plain\n");
 $smtp->datasend($body . "\n\n");

 # Send attachments
 foreach my $file (@attachments) {
     unless (-f $file) {
         die "Unable to find attachment file $file\n";
         next;
     }
     my($bytesread, $buffer, $data, $total);
     open(FH, "$file") || die "Failed to open $file\n";
     binmode(FH);
     while (($bytesread = sysread(FH, $buffer, 1024)) == 1024) {
         $total += $bytesread;
         $data .= $buffer;
     }
     if ($bytesread) {
         $data .= $buffer;
         $total += $bytesread;
     }
     close FH;

     # Get the file name without its directory
     my ($volume, $dir, $fileName) = File::Spec->splitpath($file);
  
     # Try and guess the MIME type from the file extension so
     # that the email client doesn't have to
     my $contentType = guess_media_type($file);
  
     if ($data) {
         $smtp->datasend("--$boundry\n");
         $smtp->datasend("Content-Type: $contentType; name=\"$fileName
+\"\n");
         $smtp->datasend("Content-Transfer-Encoding: base64\n");
         $smtp->datasend("Content-Disposition: attachment; =filename=\
+"$fileName\"\n\n");
         $smtp->datasend(encode_base64($data));
         $smtp->datasend("--$boundry\n");
     }
 }

 # Quit
 $smtp->datasend("\n--$boundry--\n"); # send boundary end message
 $smtp->datasend("\n");
 $smtp->dataend();
 $smtp->quit;
}

# Send away!
&send_mail_with_attachments('your_email@gmail.com', 'Server just blew 
+up', 'Some more detail','enter path to attachment here');

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[d/l]

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