I am trying to send an email from the server with an attachment using the system stored procedures xp_startsmtp and xp_sendmail.

begin
call xp_startsmtp(
smtp_sender = 'validsender@sendingdomain.com',
smtp_server = 'smtp.sendingdomain.com',
smtp_sender_name = 'SQL DB MSG');

call xp_sendmail(
recipient = 'validemail@validdomain.com',
subject = 'Hey Matt',
"message" = 'Just Checking in on you',
include_file = 'c:\\Test.txt');
end

This works when Test.txt is under a certain length like this:

abcdefghijklmno
abcdefghijk
test1
test2
test3
tes

This is either 44 characters or 49 characters depending on whether you count the new lines as characters.

Add one character to the above though to make either 45 or 50 respectively like this:

abcdefghijklmno
abcdefghijk
test1
test2
test3
test

and the message does not go through.

On a single line this works at 54 characters:

abcdefghijklmnoabcdefghijktest1test2test3test4test5tes

but this fails at 55

abcdefghijklmnoabcdefghijktest1test2test3test4test5test

Using a packet sniffer I can see the SMTP conversation and the server is responding with this:

Response: 451 see http://pobox.com/~djb/docs/smtplf.html

The website basically says that some mailers put LF at the end of lines (specifically mentioning the mailer "sendmail v8" doing this with long lines) instead of CR LF and that causes problems down the line.

The xp_sendmail procedure calls another procedure that calls a .dll, which I assume packages and sends the message with the attachment. Because it uses the .dll I do not think I can adjust the output manually by adding some CR 's somewhere.

So, is this a bug? Should I handle this differently?

Using 11.0.1.2436