User experience with PHP generated emails

[NotionCommotion]

Situation

1. User sets up an account, assigns the account a unique account name, and enters his email.  Note that user email must be unique across all accounts.
2. User then enter his contacts along with the contact's emails and assigns each contact a unique username.  Note that contact email must be unique for a given account.
3. User then selects several (typically 10 or less) contacts and sends mass email.
4. The email has a FROM email of usersName@mysite.com and a REPLY TO email of usersEmail@usersDomain.com.

Problem

1. Instead of replying to the email, email recipient copies and pastes the email displayed in his email client and generates a new email to send to the user, but the email is not delivered as usersName@mysite.com doesn't exist.

 

Possible Solutions

1. Make user educate recipients to reply to the email instead of copying and pasting the email.  Not really an option.
2. Somehow spoof the email client to display the user's real FROM email.  Is this possible and still ensure that emails are not often blocked by spam filters?
3. Make the FROM email usersName.accountName@mysite.com.  Somehow use PHP to catch them emails, and create a new email to send to the user.  Is this possible?  Would having an email such as realEmail@mysite.com no longer be possible?

[Jacques1]

Handing out fake e-mail addresses is a bad idea. Either make it clear that the user isn't supposed to use the From address (e. g. the classical noreply@yourdomain.dom). Or use real addresses on your domain which accept and forward mails.

 

I would avoid the latter at all costs, because it makes you responsible for managing potentially sensitive data and preventing spam/malware. If there's no need for that, don't do it.

Edited December 6, 2016 by Jacques1

[NotionCommotion]

The noreply@yourdomain.dom is not ideal as the email recipient should and could reply to the email using the reply-to email.  They just shouldn't reply to the from email.

 

I've always thought that when receiving such an email, a reply would go to the noreply email.  I've since tested it, and dropbox among others actually do as I wish to do and reply to the human sender, so maybe it is not so bad.

 

Thanks

[kicken]

The noreply@yourdomain.dom is not ideal as the email recipient should and could reply to the email using the reply-to email.

That's exactly what the Reply-to header is for. When the user clicks reply the email client will use the reply-to address rather than the from address. Using noreply (or similar) as the from address should make it apparent that the user shouldn't try and use that address thus stopping them from copying it to a new message. There's really not much you can do about it if someone wants to be dumb/silly and do that though.

[ignace]

What you should do though, is set up an auto-response for the noreply address. So that anyone who does decide to mail that address is informed of their mistake.