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MS Exchange does not allow sending emails from any user that is not a user in Exchange.

Which means a form on our site can't send from that user name or that user's email for replying via SMTP/Exchange.

So how can we get emails from a customer clicking Support or Sales to ask a question and actually see their name in From. As to the their email, adding a reply-to is probably OK, but seeing an inbox full of "From:Support" won't cut it.

We're on a host now where CDONTS is used and works since it's unauthenticated for sending, but this won't be an option soon.

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  • I think you are asking the wrong question. The most immediate solution might be to change your email client to show the Reply-To address as a column instead of or in addition to the From address. There should be no need to send the message from the user if you can configure your email client.
    – Stephen Ostermiller ♦
    Jun 8, 2020 at 13:18
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    And why are you using email at all for handling support requests? An email box can work well if you have one person responsible for support. However, with multiple people you need the ability for support personnel to coordinate. You don't want two people responding to the same customer. You may want prompt replies to come back to the same support agent. You'll want to build or buy a support ticketing system.
    – Stephen Ostermiller ♦
    Jun 8, 2020 at 13:21
  • @Stephen Agreed, but it's a small org here and there is one person handling support, and one sales. So works fine for us.
    – SKidd
    Jun 9, 2020 at 7:53
  • @Stephen Agreed, but it's a small org here and there is one person handling support, and one sales. So works fine for us. As to the use of a reply-to column, sure, but that's a kludge and not a fix - and also doesn't address what we want which is to have emails send from the site as the person contacting us, which works with CDONTS. Surely there a gazillion website where the business email on Exchange and can send mail from their site without resorting to a reply-to column, just asking if anyone know what the options are.
    – SKidd
    Jun 9, 2020 at 8:01

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I don't see using the "Reply-To" field as a kluge at all. This is exactly the type of situation for which it was designed.

You should not be authorized to send email on behalf of your users. A properly configured email server should reject forged email that is not sent from authorized email servers. Most domains now use DKIM, SPF, and/or DMARC that authenticate email for their domain. Any email sent by with your customer in the "From" field is not going to pass spam and forgery checks.

Since the emails are being sent to you, you are asking to carve out an exception on your own email server so that these emails don't get subjected to scrutiny. That may be possible (I don't know anything about Exchange, so I don't know how to do it), but it sounds very fragile. You would have to make sure that you can apply the same exceptions every time you upgrade your software or change email providers. At some point, that configuration is going to get break and you are going to stop getting support emails.

If you put customer email into the "Reply-To" field, pretty much everything works as you want it to.

  • The emails come from one of your own addresses using your own SMTP server, so they pass spam checks
  • The email get delivered to you
  • Replying to the email replies to the customer

The only configuration you need to do is change your email client to show the "Reply-To" address.

I'm the author of an open source contact form that works using Reply-To. Originally, I had been putting the email address of the person contacting me into the "From" field. However about ten years ago my email server started rejecting those emails. Other people who were using the contact form also noticed this problem. To fix it, the contact form simply uses the "Reply-To" field now.

I run the Thunderbird email client. I configure it to show the Reply-To field in that mailbox using the "Correspondents" column. It works beautifully:

Correspondents column in Thunderbird

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  • Starting with your "I don't know anything about Exchange" pretty much disqualifies commenting/answering. It was a question about Exchange to begin with. There is no risk to how it worked with CDONTS as in over 16 years it's never been an issue: the send to is at the server side would not be hijacked to generate spam. It's a web contact form, sends to us. Period. CDONTS doesn't authenticate the sender name/email. Also there is no reply-to column field in Outlook headers so all incoming would show from us. Sorry, this reply is so way-off that I may just post to Quora.
    – SKidd
    Jun 9, 2020 at 15:16
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    @SKidd. You have 65 reputation V Stephen's 79,700+. I, as a long time observer of his posts, suggest that you pay attention to what he is saying. FWIW, as a web host, I 100% agree with his answer - but you can look elsewhere for the same answer to confirm it.
    – Steve
    Jun 9, 2020 at 22:29
  • @SKidd is correct that I don't directly answer their question. I answered is as an XY question, suggesting they take a step back and find an alternate solution to the larger problem. Somebody here may know how to configure Exchange they way they want, but I don't think any of our regulars are Exchange experts. Most folks here have more expertise in web servers than email servers. It would probably take somebody stumbling across this question from a Google search.
    – Stephen Ostermiller ♦
    Jun 10, 2020 at 12:07
  • @steve I get your points but it all misses the point all the same as to the responses: If on a Windows server for web hosting, you're basically stuck with whatever it has as far as being able to send email from that server to us from customers. With CDONTS, one could have a web response form send the sender and show that as the from whether you use Outlook or not. Without CDONTS, all incoming mail from the server is from a user that is a member of your Exchange server, so e.g. all would incoming from Sales or Support. That is way more than sub-optimal.
    – SKidd
    Jun 10, 2020 at 16:34
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    I do take issue with "he should not have even answered on that basis alone." I don't have the experience to give you the direct answer you are fishing for, but I do have plenty of experience with contact forms and reply-to and could formulate an answer that addresses your underlying problem. You have rejected it out of hand, which is your right, and you don't need to accept it. However, it is fine to have it here. It may help future visitors with similar issues and it doesn't prevent other people from providing other answers.
    – Stephen Ostermiller ♦
    Jun 16, 2020 at 15:43

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