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I send email notifications on behalf of my customers to their customers (tertiary customers). Sometimes my tertiary customers respond to those emails with the expectation that it will reach my customers.

What strategies can be used to prevent this from happening, or to educate the tertiary customers?

When i receive emails from my tertiary customers, I could auto reply informing them that their email has not reached the intended recipient. However I am concerned that this may result in an infinite email loop if they happen to have an out of office auto-responder.

If it is relevant, my email provider is google apps.

pingu
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    Typically be setting a `Reply-To` header in the email you send with the relevant email address of your customer... – HBruijn Oct 10 '14 at 10:39
  • @HBruijn - Thanks for the reply, unfortunately that is not an option as my customers use it for broadcast only. It is a requirement that they cannot be contacted using it. – pingu Oct 10 '14 at 11:38

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It is not uncommon to use a header with something like Reply-to: No Reply and a similar warning in the actual message.

It depends a bit on the actual e-mail client how it deals with a Reply-To field without a valid email address though. Some will generate a reply with that No Reply in the field of the recipient, but hitting send will of course fail as that's not a valid recipient address. Other mail clients will generate the reply with an empty To: field and still others will simply use the From: address when the Reply-To header is invalid.

Better to include a email address as well in the Reply-To: header then and not be reliant on the quirks of e-mail clients...
Use Reply-to: No Reply <noreply@example.com>. If the recipient still replies despite the big hint in the To: field of their email message your options are then to either accept and silently discard all messages for that mailbox. Or alternatively if you're running your own incoming mailserver, generate a SMTP error with a message reminding them that it is an unattended mail address.
SMTP errors should not trigger infinite loops.

HBruijn
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