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2643

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6

My web application sends email fairly often, and it sends 3 kinds of emails: initiated by user, in response to an event in the system, and in automatic response to an email received by the application.

I would like to make sure that the third type of email does not get stuck in an endless loop of auto-responders talking to each other. Currently, I use the header:

Precedence: junk

but Yahoo! mail is treating these messages as spam. This is obviously not ideal, because we would like SOMEBODY to read our auto-response and make a decision on it, just not an out-of-office reply.

What is the best way to send an email without triggering either junk filters or auto-responders?

Precedence: junk?

Precedence: bulk?

Precedence: list?

X-Priority: 2?
A: 

Spam filters usually look at the entire message, to determine spaminess. Good luck getting past that one.

As far as out-of-office replies, I think the only way to not trigger them (Outlook specific, and I may be wrong), is to not send the message directly to the Out-of-Office person. Obviously, you may not know that at the time, so that may not be a solution.

gms8994
A: 

How about configuring a white list on your email account?

I would assume that any email key words could get flagged by a junk filter.

Robert
I can't go to Yahoo! and tell them to put my application on a white list, if that's what you meant.
Jacob
+1  A: 

The traditional way of dealing with this is to send the email with a null envelope-sender (traditionally written as <>). This prevents the autoresponder on the other end from responding because there's no sender to respond to.

jj33
+4  A: 

RFC 2076 discourages the use of the precedence header. as you have noted, many clients will just filter that off (especially the precedence: junk variety). it may be better to use a null path to avoid auto responder wars:

Return-Path: <>

Ultimately you could use priority to try to get around this, but this seems like going against the spirit of the header. i'd suggest just using the return-path header for this, and avoiding precedence. in some cases you may have to write in some way to drop auto-responders in your application (to avoid getting into a responder war), but i can't remember a situation in which this happened using an appropriate return-path. (most auto responder wars i recall having to deal with were the result of very badly formed emails)

Note: the Return-Path header is, in short, the destination for notifications (bounces, delay delivery, etc...), and is described in RFC 2821 -- because it's required by SMTP. It's also one method to drop bad mail (as theoretically all good mail will set an appropriate return-path).

Owen
Can you explain what Return-Path is used for? (I assume it's much different than the Reply-To header)
Michael Pryor
in short it's the destination for notifications (bounces, delay delivery, etc...), and is described in RFC 2821.because it's required by SMTP, it's also one method to drop bad mail (as theoretically all good mail will set an appropriate return-path)
Owen
+4  A: 

There is a RFC 3834 dedicated for automated email responses.

In short, it recommend:

  1. Send auto-responses only to address contained in Return-Path header of incoming message, if it is valid email address. Particularly "<>" (null address) in Return-Path of the message mean, that auto-responses must not be send for this message.

  2. When sending auto-response, MAIL FROM smtp command must contain "<>" (null address). This would lead to Return-Path:<> when message will be delivered.

  3. Use Auto-Submit header with value other then "no" to explicitly indicate automated response.

One note: it is not worth to explicitly set Return-Path header in outgoing message, as this header must be rewritten by envelop address (from MAIL FROM smtp command) during delivery.

A: 

whenever i am giving the From Name and from Email id in the Email header then the email could not delivered. but when i remove these two information then email going properly.

i am using $headers = "From:My Name here\nContent-Type: text/html; charset=iso-8859-1;";

what may be the problem?

Thnx in advance.

virendra kumar