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 test@mydomain.ca, 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=<test@mydomain.ca>, 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=<SRS0=brxw=GC=gmail.com=myemail@gmail.com>
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=<SRS0=brxw=GC=gmail.com=myemail@mydomain.ca>, size=4544, nrcpt=1 (queue active)
Dec 30 23:05:57 vps-1234 postfix/smtp[21532]: EAFA74B7E5: to=<myemail@gmail.com>, 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 gmail.com=myemail@mydomain.ca that is a weird made up email that I think should either be test@mydomain.ca or myemail@gmail.com, 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)
