Issue Forwarded Email marked as SPAM by GMAIL

[jenjohn]

Server operating system version

Ubuntu 22.04

Plesk version and microupdate number

18.0.57

Hi,

Even though I am brand NEW to Plesk, I was able to setup multiple WP websites with emails, DNS lookup etc. Got _DMARC and other requirements correct also. When I send a email from one of the domains hosted in Plesk, it goes straight to Inbox of GMAIL! Yay!

One of the non-profits wanted to setup ALIASES (for info@nonprofit.org, aliases were contact@nonprofit.org, ask@nonprofit.org etc). All of the emails that comes to either the aliases or the original info should be forwarded to an external email (Gmail, Yahoo, Outlook.com etc). So I setup a FORWARDING email option to all of them. That is where trouble started. Irrespective of incoming email to info (original) or contact/ask (aliases), the forwarded email lands in SPAM folder.

When I send an email directly to external email, it goes to their Inbox. Only when forward happens, it gets flagged as SPAM. I have instructed them to create address entries but we will be creating a lot of aliases and there are a lot of volunteers in the nonprofit. Is there any way to make sure that forwarded email doesn't drop into the spam folder?

I think it is not fair by Gmail/Yahoo etc to mark all forwarded email as spam! These are legitimate uses.

 

[Peter Debik]

The problem with forwarded mails is that the IP address of the forwarding server is not part of the SPF entry of the sender, so the forwarder is not authorized to send or relay domain on behalf of the sender. This triggers GMail to think it's spam. At the moment there is nothing one can do about it but to stop the normal forwarding and replace it with a kind of incoming mail rule, meaning mail is received by a client and forwarded as new mail from that client as if it was originally sent by the client.

 

[rdadmin]

Hi, any solution to this? i can't found a way to redirect as new mail to fullfill the spf requeriments whith external antispam. Thanks

 

[jenjohn]

Plesk may be able to solve it (if I understand Peter correctly) if Plesk sends the IP address of the forwarding server (Plesk in this case) also in the SPF entry.

 

[Aslanj]

(using 18.0.65 now)
I wanted to bump this thread as it continues to be an issue for us. Emails forwarded to Google-hosted addresses can be marked as spam.

Our DNS settings (i.e., DKIM, DMARC, SPF) appear to be working fine, and I can see ARC sealing is also functional on the Plesk side. However, one issue I continue to see is the body hash verification failing. This appears to be due to how Plesk either very slightly modifies the content (even a different linebreak) or re-encodes it, which changes the hash the receiving end calculates, even though ARC seal is in place.

Any suggestions or insight would be most welcome.