my $to          = qq|"Andy" <andy.newby@gmail.com>|;
my $subject_val = "test subject";

my $write_path = "/srv/www/mysite.net/www/cgi-bin/admin/invoice_pdfs/new/pdf_versions/$order->{amazon_order_id}.pdf";
my $file_name  = "$order->{amazon_order_id}.pdf";

if (!-e $write_path) {
    print qq|PDF doesn't seem to exist yet! SKIPPING ($write_path) n|;
    next;
}

print "TO: $to n";

my $to          = qq|"$order->{buyer_name}" <andy.newby@gmail.com>|;
my $subject_val = sprintf($languages->{subject}->{$lang},$order->{amazon_order_id});

my $write_path = "/srv/www/mysite.net/www/cgi-bin/admin/invoice_pdfs/new/pdf_versions/$order->{amazon_order_id}.pdf";
my $file_name  = "$order->{amazon_order_id}.pdf";

my $msg = MIME::Lite->new(
    Type     => 'multipart/mixed',
    Subject  => $subject_val,
    To => $to,
    From => $from
);

# create a sub-part
my $part = MIME::Lite->new(
    Type => 'multipart/alternative',
);

my $att_html = MIME::Lite->new(
    Type     => 'text',
    Data     => "text version",
    Encoding => 'quoted-printable',
);
$att_html->attr('content-type' => 'text/plain; charset=iso-8859-1');
$part->attach($att_html);

my $att_text = MIME::Lite->new(
    Type     => 'text',
    Data     => "html version",
    Encoding => 'quoted-printable',
);
$att_text->attr('content-type' => 'text/html; charset=iso-8859-1');
$part->attach($att_text);

$msg->attach($part);

$msg->attach(
     Type     =>'application/pdf',
     Path     => $write_path,
     Filename => $file_name,
     Disposition => 'attachment'
);

my $email = $msg->as_string();

# now do the sending...
my $smtp = Net::SMTP->new('smtp.gmail.com',
                       Hello => 'steampunkjunkies.net',
                       Timeout => 30,
                       Debug   => 1,
                       SSL     => 1
                      ) || die "Error: $!";

$smtp->auth($CFG->{db_smtp_user}, $CFG->{db_smtp_pass}) or die "Could not authenticate with mail.n";

$smtp->mail($from); # from addr
$smtp->to($to);
$smtp->bcc('myemail@gmail.com');
$smtp->data($email); # It hangs here
$smtp->quit();

$msg->attach(
     Type     =>'application/pdf',
     Path     => $write_path,
     Filename => $file_name,
     Disposition => 'attachment'
);

perl -d test.cgi

Loading DB routines from perl5db.pl version 1.44
Editor support available.

Enter h or 'h h' for help, or 'man perldebug' for more help.

Malformed UTF-8 character (unexpected non-continuation byte 0x63, immediately after start byte 0xe9) at test.cgi line 24.
 at test.cgi line 24.
"my" variable $to masks earlier declaration in same scope at test.cgi line 87.
 at test.cgi line 87.
"my" variable $subject_val masks earlier declaration in same scope at test.cgi line 88.
 at test.cgi line 88.
"my" variable $write_path masks earlier declaration in same scope at test.cgi line 90.
 at test.cgi line 90.
"my" variable $file_name masks earlier declaration in same scope at test.cgi line 91.
 at test.cgi line 91.
IO::Socket::SSL::CODE(0x29d3f50)(/usr/local/share/perl/5.20.2/IO/Socket/SSL.pm:192):
192:            INIT { init() }
                                                                                                                                                                                                                                               DB<1> r
void context return from CODE(0x29d3f50)
main::(test.cgi:14):    $| = 1;
                                                                                                                                                                                                                                               DB<1> r
Content-type: text/html; charset=utf-8

Doing: 205-2876651-1862762
TO: Indrek Päri
$VAR1 = 'Indrek Päri';
TO: "Andy" <andy.newby@gmail.com>
r



^X^CIO::Socket::SSL::readline(/usr/local/share/perl/5.20.2/IO/Socket/SSL.pm:1171):
1171:           if ( ! defined $poke or $poke eq '' ) {

DB<1> n
^CIO::Socket::SSL::readline(/usr/local/share/perl/5.20.2/IO/Socket/SSL.pm:1171):
1171:           if ( ! defined $poke or $poke eq '' ) {