I need to send an email with an attached .pdf file. I am able to send the attcahed file using uuencode as follows (script1) :

ATTFILE=/home/user/test.pdf
ATTNAME=test.pdf
MAILTO=my.receiver@xxx.com
MAILFROM=my.sender@xxx.com

uuencode $ATTFILE $ATTNAME | sendmail -v f${MAILFROM} ${MAILTO}

This code delivers the attached file correctly to my.receiver@xxx.com,
however it ends up in Spam mail with :

From: my.sender@xxx.com
To:
Cc:
Subject:
Attachments : test.pdf

This is doing everything I need, except putting my.receiver@xxx.com in the To: line of the email, which apparently is causing it to end up as SPAM, yet the email does end up at my.receiver@xxx.com's email. Go figure ?

SO the I tried the following (script2) :

ATTFILE=/home/user/test.pdf
ATTNAME=test.pdf
MAILTO=my.receiver@xxx.com
MAILFROM=my.sender@xxx.com

TEMPFILE=tempmail.txt
echo"From:${MAILFROM}\nTo:{MAILTO}\nCc:\nSubject:\n" > TEMPFILE

uuencode ${ATTFILE} ${ATTNAME} | sendmail -t -oi < ${TEMPFILE}

This puts all of the information in the email address lines, and delivers the mail to my.receiver@xxx.com's inbox, but no attachement :

From: my.sender@xxx.com
To: my.receiver@xxx.com
Cc:
Subject:
Attachments :

I need to force the To: line in script1, or make the attachment work
in script2.

Any Ideas ?

Do you have reason to believe that you can second-guess the recipient's spam filter, or do you know for a fact that this will solve your problem?

Try filling in more of those fields; empty Subject lines trip some spam filters, too. script2 is apparently an attempt at solving this, but uses invalid syntax -- you can't both pipe to sendmail and have it read a file. See a fix below.

uuencode is pretty ancient; perhaps you can find a tool which would allow you to send a proper MIME attachment. I don't think this has any bearing on the spam filtering, but a proper tool would feel a lot less crippling and give you more control over what is sent.

ATTFILE=/home/user/test.pdf
ATTNAME=test.pdf
MAILTO=my.receiver@xxx.com
MAILFROM=my.sender@xxx.com

( cat <<HERE; uuencode "${ATTFILE}" "${ATTNAME}" ) | sendmail -oi -t
From: ${MAILFROM}
To: ${MAILTO}
Subject: attached $ATTNAME

HERE

Hi, I tried the script, but the attachment is part of the mail body, and is "non readable" (unencoded text enclosed by begin and end identifiers). I was expecting an e-mail with the text file as an attachment. What have I missed ?

I have tried several different text files.

Thanks for any help :-)

Like I wrote above, uuencode is not a valid MIME attachment; in fact, MIME was invented in part to overcome the limited usability and modularity problems of inlining uuencoded binaries into the main mail message. The MIME framework provides a facility for messages with multiple parts ("multipart") some of which can have a content-disposition of "attachment".

Having said that, some sending programs recognize uuencode, and transform the message to MIME on the fly; and some receiving programs recognize uuencode, and display it as an attachment, even though it's technically just a blob of text inlined into the human-readable mail body.

The FAQ section has several scripts for sending proper MIME attachments. The easiest is probably if you have mutt or a reasonably recent elm or pine, but if those are not an options, check out the scripts over here