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This happens a lot, in our work email system, which uses Gmail and various internal email groups:

  • I receive an email to helpdesk@example.com, from Alice <alice@foomail.com>
  • I forward it to bob@example.com
  • in Bob's email, he can see the original message subject and body, but the From just says "Alice": it's lost the actual email address.

Even if you look at the actual email data, in the "Show Original" option, it's gone.

Does anyone know if there's a setting in Gmail to stop this happening?

EDIT: here's a screenshot. I've just noticed the "Via Helpdesk" bit, I wonder if that's part of the problem.

EDIT: Added another screengrab showing how the original appears.

This is how the original looks:

enter image description here

This is what the "forward" email looks like.

enter image description here

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    What procedure are you using to forward emails? Are you using the GMail website or another mail client? – binki May 15 '17 at 16:23
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    In GMail when I click “Forward”, it generates text like ---------- Forwarded message ---------- followed by From: Example <alice@example.com>. When viewing in GMail, if I hit the “…” in the received message, I see the exact text as I saw when I was composing the message. Maybe if you could show screenshots of what’s happening it’d be clearer? – binki May 16 '17 at 15:15
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    It appears that your helpdesk system is itself receiving emails from the user and then resending them to GMail. To avoid being rejected by SPF filters, helpdesk is using its own email address as the From and only saving the freeform name of the sender. Before you forward the message, how does it show you the original sender’s email address? IMO, the best way to handle this is to forward as attachment instead of inline forward. I don’t know if GMail’s web interface offers forward as attachment, but I know e.g. Thunderbird can. Attachment/MIME forwarding will save the entire message. – binki May 17 '17 at 17:41
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    webapps.stackexchange.com/q/16434 discusses how to do MIME attachment-style forwards in GMail, but it’s a really complicated, impractical process when just using the webapp interface to GMail. – binki May 17 '17 at 17:48
  • @binki - you're right, I think: it looks like it is forwarded on from our email server, which puts its own address into the From, and it keeps the original sender's email in the Reply-to header. I will speak to the guy who manages our email server, maybe he has an idea about how to better handle it. I wonder if he can get it to just write "From: <original sender email>" into the top of the body or something. – Max Williams May 18 '17 at 9:13
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From the pictures and updated information, Gmail is forwarding the email inline. Vanilla Gmail appears to only support forwarding emails inline. When emails are forwarded "inline", only a small amount of information from the original email is preserved. As shown in the pictures, the headers From, Date, Subject, and To are extracted from the original message and rendered in text form in the inline-forwarded email.

The technique your helpdesk system uses for forwarding emails replaces the From with helpdesk's own email address. This is necessary because otherwise Gmail's SPF policies would cause it to reject the mail or immediately mark it as Spam/Junk. Since your helpdesk system puts the original sender's email in Reply-To, you can still reply to those messages to reply to the original sender. However, if you forward the email inline, Gmail's inline-mail-header-formatter will not copy the Reply-To header because it just doesn't. That is, Gmail is keeping the From; it is your own internal system that is losing the From before the message gets to Gmail. And Gmail does not preserve Reply-To.

Now, it is possible to forward emails as MIME attachments in Gmail. If you did this, the receiver of the forwarded email would be able to see the original Reply-To header of the attached email. However, this is an involved and impractical process because Gmail's web interface is not able to do the work for you. I would suggest using Gmail's feedback feature to request support for forwarding emails as MIME attachments (as this is a standard feature in desktop mail clients). Another option is to set up a desktop email client (but that solution is outside the scope of "WebApps”, hmm…) with Gmail since it will not have this limitation.

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    Thanks - looks like there isn't a practical solution (forwarding as attachments will be too much hassle I think). I will speak to the person who runs our mail server and see if they have any ideas. cheers – Max Williams May 19 '17 at 8:14

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