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I have a VPN configured with Plesk.

(I have installed a SSL/TLS certificate, through Plesk, using Lets Encrypt. Everything seems good as far as I can tell, but I mention it as it also protects emails.)

I have setup a mail forward, without a mailbox.

To test it, I use my GMail account to send an email to the [email protected], which should be forwarded back to the same GMail I sent it from.

This the tail of /var/log/maillog:

Dec 30 23:05:55 vps-1234 journal: plesk sendmail[21517]: handlers_stderr: SKIP
Dec 30 23:05:55 vps-1234 journal: plesk sendmail[21517]: SKIP during call 'check-quota' handler
Dec 30 23:05:55 vps-1234 postfix/pipe[21511]: 7A3BC4B7E3: to=<[email protected]>, relay=plesk_virtual, delay=1.5, delays=0.72/0.02/0/0.76, dsn=2.0.0, status=sent (delivered via plesk_virtual service)
Dec 30 23:05:55 vps-1234 postfix/qmgr[21455]: 7A3BC4B7E3: removed
Dec 30 23:05:55 vps-1234 postfix/pickup[21454]: EAFA74B7E5: uid=30 from=<[email protected]>
Dec 30 23:05:55 vps-1234 postfix/cleanup[21501]: EAFA74B7E5: message-id=<CAAg_DarPpmMvHyar=2xYDHNE6w-UeKQfPSuUMfgyG44xzFY8Dg@mail.gmail.com>
Dec 30 23:05:55 vps-1234 postfix/qmgr[21455]: EAFA74B7E5: from=<[email protected]>, size=4544, nrcpt=1 (queue active)
Dec 30 23:05:57 vps-1234 postfix/smtp[21532]: EAFA74B7E5: to=<[email protected]>, relay=gmail-smtp-in.l.google.com[74.125.192.26]:25, delay=2, delays=0.02/0.02/0.54/1.4, dsn=2.0.0, status=sent (250 2.0.0 OK  1609369557 h6si28285381qth.374 - gsmtp)
Dec 30 23:05:57 vps-1234 postfix/qmgr[21455]: EAFA74B7E5: removed

I noticed the [email protected] that is a weird made up email that I think should either be [email protected] or [email protected], but it seem the email is sent properly...

Yet it is not in my Inbox or my Spam folder on GMail. Any ideas ?

Edit1:

Following the comment confirming Google did received my email, I have added the domain on https://postmaster.google.com. The domain is validated, but there is no data being displayed.

I have also ran the domain through https://mxtoolbox.com/emailhealth/ and I do have the following warnings:

dmarc   mydomain.ca DMARC Quarantine/Reject policy not enabled
mx      mydomain.ca DMARC Quarantine/Reject policy not enabled
smtp    mail.mydomain.ca    Reverse DNS does not match SMTP Banner

I am currently trying to resolve the last one, but as I understand none of those warnings should justify the email not being delivered.

Currently the SMTP banner is:

$ telnet localhost 25
Trying ::1...
Connected to localhost.
Escape character is '^]'.
220 mydomain.ca ESMTP Postfix

My current thesis is that the domain and IP is new and might not have a good reputation enough yet, but I currently have no way to confirm that yet (as postmaster is not displaying anything)

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  • 2
    You'll have to take it up with Google. They accepted your mail for delivery. Dec 31, 2020 at 3:04
  • @Michael Hampton: is it possible something is wrong on my server that makes it look like a spam so bad it doesn't even get to the Spam folder and just get deleted? --- and when you say "take it up with Google", is it a joke about their lack of support or is there actually something I can investigate about it?
    – FMaz008
    Dec 31, 2020 at 4:08
  • 2
    It's no joke. Google accepted your mail. If you want to know what happened after that, only they can help you. Dec 31, 2020 at 4:42

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