I built a web-based application where the user enters his or her business associates' name and email, and can then compose a single message and send it to all of them at once (the messages are automatically parsed with the recipients name, etc, and typically sent to around 5 people at once). The recipients should be able to reply to the email, and it should go to the original user's email.

A bit of background history. Note that these mini-mass emails are not being sent from from the user's email client, but are being sent from my server which the user access via a web browser. This represents a little technical challenge. To prevent email abuse, many email servers will not accept emails which the FROM email doesn't match the server which sent it. To get around this, email technology allows both a FROM email and a REPLY-TO email.

So, if "John Doe" is the user who is sending out the emails, the recipients will receive an email which is from John Doe [[email protected]], but when they reply to it, it will go to [email protected].

I thought all was good, but then found that some recipients didn't reply to the email, but copied the email and posted it into a new email, and it incorrectly goes to [email protected] instead of [email protected]. To help a little bit, [email protected] returns an auto-reply explaining the mistake.

So what to do? The common solution is to make the FROM email John Doe [[email protected]] and keep the REPLY-TO email as [email protected]. I looked at Drop Box, and they do John Doe (via Dropbox) [[email protected]], and if one replies to it, it will go to [email protected] (note that most others only reply to [email protected]. But in my opinion, this seems to imply that the recipient shouldn't reply to the email, yet the behavior I am trying to promote is for them to reply to the email.

How can I make it obvious that one can reply to an email yet not send an email to the FROM email?

  • I downticked your question because improving the ability to spam doesn't seem like a good (ethical) task for HF.
    – MMacD
    Commented Dec 8, 2016 at 12:08
  • 2
    @MMacD It is not spam. The sender knows every recipient and each recipient is expecting an email from the sender. The application is a proposal submission tool. A typical reply is "Got your proposal John. Thanks". Commented Dec 8, 2016 at 14:00
  • I continue to feel that the whole thing seems dodgy at best. Why is your site involved at all, if it's a tiny RFP list? Why doesn't the requestor's admin staff do the responding?
    – MMacD
    Commented Dec 8, 2016 at 19:16
  • 1
    @MMacD Who has an admin staff now a days? And it is typically to have several proposals each day which need to be submitted. And while I appreciate your interest, I am not asking about the need for a proposal distribution system, but only how to communicate to the recipients that they can reply to an auto-generated email. Commented Dec 8, 2016 at 23:51

1 Answer 1


Here are some ways to handle alternative recipient responses in relation to server proxied email communications:

A. Write script to handle the "cut and paste email in a new message" dilemma:

Dynamically generate a unique email address for each communication sent. In the case of John Doe <[email protected]> initiating communication generate:

john.doe%[email protected]

Along with that write a catchall script that watches incoming email to *@forward.mysite.com, parses the username, and forwards the message to [email protected].

If John sends out a lot of these and there may be different purposes, then keep track of the details of each particular communication in a database and tag it with a unique ID, such as 8woeiEIuei29A23uius. Then use the unique ID for the username portion of email: [email protected], and use the script to parse that and grab the communication particulars and append to the message before returning the email to the initiator.

B. Provide a clear response path in the initial message body:

Additionally, provide a clear method for the recipient to respond to the initiator in the body of the initial message. For example:

Greetings Richard Roe,

Here's the information you requested I send you through this cool middleman site mysite.com. If you desire to respond to me click here:

Respond to John Doe

Or if you wish to send a message to mysite.com click here:

Respond to mysite.com

Best wishes,
John Doe (by way of mysite.com)

Then if Richard clicks either button you can either bring him to mysite.com or use a mailto: link to direct his email client to generate a new message to the return dynamically generated email address.

  • Good recommendations! Let me think it over. Thanks Commented Dec 10, 2016 at 2:00

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