Issue Notification emails from psaadm when checking for updates are being blocked.

[pick3pro]

Hello,

I have had a VPS server (Ubuntu) up and running with Plesk since June 2021. With one of the updates for 18.0.40 around the middle of January, 2022 I noticed I was no longer receiving email notifications from psaadm informing me of updates. My admin email address is a gmail address. When I look in the maillog files I see the following entries for Feb-2022

For posting the logs to this forum I changed my real gmail address to [email protected] and my real domain name to vps.mydomain.com.

I am hosting on Vultr and pretty sure only ipv4 is configured. I don't remember seeing network is unreachable before and don't know why its trying ipv6. I don't see any of these errors prior to plesk being auto-updating I believe on Jan-11-2022.

Why would google relay be blocking an email from psaadm ??? I have also seen it block emails from [email protected]

Feb 16 06:25:39 vps plesk-sendmail[2423]: S2423: from=<[email protected]> to=<=?UTF-8?Q?admin?= <[email protected]>>
Feb 16 06:25:39 vps plesk-sendmail[2424]: S2423: add-from: stderr: SKIP
Feb 16 06:25:39 vps plesk-sendmail[2424]: S2423: check-quota: stderr: SKIP
Feb 16 06:25:39 vps postfix/pickup[28037]: 88056FE7E0: uid=999 from=<psaadm>
Feb 16 06:25:39 vps postfix/cleanup[2432]: 88056FE7E0: message-id=<[email protected]>
Feb 16 06:25:39 vps postfix/qmgr[31312]: 88056FE7E0: from=<[email protected]>, size=12310, nrcpt=1 (queue active)
Feb 16 06:25:39 vps postfix/smtp[2438]: connect to gmail-smtp-in.l.google.com[2607:f8b0:4023:1407::1b]:25: Network is unreachable

Feb 16 06:25:40 vps postfix/smtp[2438]: 88056FE7E0: to=<[email protected]>, relay=gmail-smtp-in.l.google.com[142.251.4.27]:25, delay=1, delays=0.02/0.01/0.32/0.66, dsn=5.7.1, status=bounced (host gmail-smtp-in.l.google.com[142.251.4.27] said: 550-5.7.1 Our system has detected that this message is 550-5.7.1 likely unsolicited mail. To reduce the amount of spam sent to Gmail, 550-5.7.1 this message has been blocked. Please visit 550-5.7.1 Why has Gmail blocked my messages? - Gmail Help 550 5.7.1 for more information. t6si16148475ywt.96 - gsmtp (in reply to end of DATA command))

The link Google provides is useless and have seen it in the past when it appears your IP address is being blacklisted. My IP address was clean and tested with 10 different gmail addresses before this. Now all of a sudden any email sent to gmail is either going to spam folder or if it's a Plesk notification it's blocked. The last time I tested this was beginning of January and everything was working in emails sent to gmail addresses were not going to spam folder and not being blocked. It makes me think that the plesk system update broke something but I am not savvy enough to know what. It sucks now because I only spun up this VPS to add a forum community to support my iOS apps. They have to register to join forum and now those registration emails will be going to their spam folder.

Did a system update change PostFix configuration or Sendmail configuration that is not compatible with Google/Gmail relay ???

Thanks for any help or enlightenment anyone can provide.

Jimmy

 

[victorjqv]

same problem after upgrade to 18.0.42

 

[pick3pro]

For me lately the emails have been going thru. Not sure what changed. As previously stated my plesk admin account is setup to use an external gmail address.

It seems like there is some type of email aliasing going on in the header when admin emails are sent from plesk to my gmail account. The email header is showing the following (I changed my email and domain name for posting reasons)
To: admin <[email protected]>
Subject: <vps.somedomain.com> Package Update Manager notification
Date: Wed, 02 Mar 2022 06:25:50 -0700
From: admin <[email protected]>

There seems to be some aliasing going on where psadm emails get mapped to my admin email for both from and to header where they are both my gmail address. When I was receiving the emails on my iphone it didn't show as anything out of the ordinary. When I recently went and looked at the emails from desktop then Gmail UI on the desktop was flagging the emails as suspicious in possible spoofing going on. In fact the emails come thru as from "me" in the UI. I went thru and marked all these emails as not suspicious and I don't know if they caused things to start working again or not. Not sure why this strange email header aliasing is going on from Plesk but it seems wrong.

I also see this in the header
spf=pass (google.com: best guess record for domain of [email protected] designates xxx.xxx.xxx.xxx as permitted sender) smtp.mailfrom=[email protected];
dmarc=fail (p=NONE sp=QUARANTINE dis=NONE) header.from=gmail.com

I read somewhere this failure sometimes happens if SPF passes with different domain than dmarc
i.e. SPF has [email protected] but dmarc thinks it's admin <[email protected]>
something about the domain names not being aligned.