Issue Mail from Plesk always spam

[MSD]

Server operating system version

Ubuntu 22.04

Plesk version and microupdate number

Plesk Obsidian 18.0.51

Hello,

I really try everything that I find in the documentation and forums, but my mail from Plesk always ends up as spam.
In this case, first is mail from Plesk itself: updates, information, and so on. I have Let's Encrypt SSL for Plesk and Mail (I get spammed mail).
The second case is mail that was sent from Wordpress or WooCommerce from a domain that has a DNS certificate (customers get spam mail).
The III case is mail sent from the Laravel app (customers get spam mail).
I try with mail from the Plesk domain, then I try with mail from the domains of WordPress and Laravel, then I try with gmail, and every time customers get SPAM.

Where is the root of the problem?

Thanks in advance...

 

[Peter Debik]

Plesk is not responsible if your mails go into spam. Plesk is a graphical user interface that helps you to configure your server properly. If your server is not configured correctly, mails may be seen as spam.

To find out more about what other systems think about mail that is sent from your domain, maybe you can use Newsletters spam test by mail-tester.com . Simply send a test mail to the address they show you, then check the results there.

 

[MSD]

Hello,

It is okay. But, I was made a fresh Plesk install on a brand new server with Debian 11 (latest release + all updates).
After all, I give a Plesk admin email our business gmail account and dedicated domain.
Now I get spam mail from Plesk about some updates and the latest releases.
So, what is wrong with gmail and a fresh install of Plesk?
Plesk is just a graphic interface with some great tools behind it, but I don't understand this situation...

 

[Peter Debik]

Now I get spam mail from Plesk about some updates and the latest releases.

You can configure which notifications admins receive in Tools & Settings > Plesk > Notifications

So, what is wrong with gmail and a fresh install of Plesk?

Nothing is wrong, everything is perfectly fine.

 

[MSD]

Hello,

The root of the problem is spam (mail that goes to spam from Plesk). I have no problem getting informational mail from Plesk.
Is there any configuration for server, domain, IP, Debian (or some other OS), Plesk, mail function in Plesk such that mails from Plesk are not spammed?

Thanks in advance...

 

[Peter Debik]

Could you please be more precise what "mail from Plesk" is for you? Above you mention all kinds of sources, e.g. Woocommerce, Wordpress, Plesk notifications. Then again you said to the mail-tester.com test results "It is okay". What is "okay" for you? 10/10 points?

 

[MSD]

Every email sent from a server that has Plesk Panel goes to spam, no matter if it's from Plesk itself (as a notification or reminder) or from, for example, a WordPress, WooCommerce, or Laraval app.
My question was, Is there any option that I missed to set to prevent this situation?

 

[Peter Debik]

What is the result of mail-tester.com?

 

[Alakide]

Hello, I have the same problem.

Every email sent by Plesk to me goes to spam... Example my plesk server send an email with a summary of the latest server updates available, then the email reach to SPAM folder... Another example, I send an email to X recipt with the option to inform me that the mail arrived satisfactorily, then, the [email protected] returns to me a notification that said that the mail arrived satisfactorily to the recipt... This email also reach to SPAM folder.

I've whitelisted the server hostname in all the anti-spam filters in the server and in my email account but the result is always the same.

I was wondering if you have any idea of whats going on?

Regards
Emmanuel

 

[Maarten]

Try to investigate the mail headers from the emails that went to the Spam folder. That should give you an insight into this issue.

For example, this is how you do this in Gmail:

Trace an email with its full header - Gmail Help

You can check the full header of an email you received from a Gmail account to know where it's from. View & copy the full header of an email Gmail From a browser, open

support.google.com

Check the status of DKIM, DMARC, and SPF. Those should have the status 'PASS'

 

[Alakide]

Try to investigate the mail headers from the emails that went to the Spam folder. That should give you an insight into this issue.

For example, this is how you do this in Gmail:

Trace an email with its full header - Gmail Help

You can check the full header of an email you received from a Gmail account to know where it's from. View & copy the full header of an email Gmail From a browser, open

support.google.com

Check the status of DKIM, DMARC, and SPF. Those should have the status 'PASS'

Thank you very much for your answer.

Actually... The emails sent from the servers come with no SPF and DKIM information, here the logs...

5B1913412E8: DMARC: smtpdomain= maildomain=server2.mycompany.com [email protected] stamp=1684170054 ip=unknown adkim=relaxed aspf=relaxed p=QUARANTINE sp=UNSPECIFIED pct=100 align_dkim=fail align_spf=fail spfres=unknown dkimres=unknown dmarccheck=DMARC_POLICY_QUARANTINE dmarcstatus=DEFER

S2102964: py-limit-out: stderr: INFO:__main__:Setting 'X-PPP-Vhost' header to 'server2.mycompany.com'

service=lda, [email protected], ip=[]. sieve: msgid=<[email protected]>: stored mail into mailbox 'INBOX.Spam'

Every notification sended by my server use the server's name, in this case server2.mycompany.com. The log information says that the domain does not have the SPF and DKIM records, but the domain mycompany.com have the correct SPF and DKIM records, we use this domain. It is worth mentioning that this domain is configured on another server where we have the DNS configuration because we use it to control different services because we have several servers on service for example for our servers we use the number of the server in the subdomain.
server1.mycompany.com points to 1.1.1.1. it's the server name for this server.
server2.mycompany.com points to 1.4.5.1 ...
server3.mycompany.com points to 2.1.3.1 ...

I have 8 servers with plesk and this issue just happends with "server2" all our servers are working with Plesk Obsidian 18.0.52 Update 2 | Ubuntu 22.04.5 LTS | Nginx 1.20.2 | Apache2 2.4.41 | Postfix 3.4.13 | Dovecot 2.3.19.1 | Warden Anti-SPAM 3.04-1


Thanks again
Regards
Emmanuel

 

[Peter Debik]

Every notification sended by my server use the server's name, in this case server2.mycompany.com. The log information says that the domain does not have the SPF and DKIM records, but the domain mycompany.com have the correct SPF and DKIM records, we use this domain.

Does server2.mycompany.com has an SPF record, too?

 

[Alakide]

Does server2.mycompany.com has an SPF record, too?

Yes, it have SPF record and everything is correct on DNS settings.

Regards
Emmanuel

 

[Peter Debik]

The log information says that the domain does not have the SPF and DKIM records, but the domain mycompany.com have the correct SPF and DKIM records

Could you please show where the log says the SPF and DKIM records are missing and also please show the MX and SPF entries for server2.mycompany.com?

 

[Alakide]

Could you please show where the log says the SPF and DKIM records are missing and also please show the MX and SPF entries for server2.mycompany.com?

Thank you for your answer.

Actually everyting is correct, this situation started when the server was upgraded from Plesk 18.0.49 to Plesk 18.0.50, now system is working on Plesk 18.0.52 and this issue remains.

Attached you can find the images of the configuration and logs

Regards
Emmanuel D

 

[Maarten]

There have been a couple of changes in Plesk 18.0.50 regarding DMARC, DKIM, and SPF:

• New domains now sign outgoing mail with DKIM. This improvement protects against email spoofing.
  
  DKIM helps to verify that an email was indeed sent from the domain and no one tampered with the email content in transit. Previously, DKIM was not enabled by default for domains. Spoofed email messages with ‘From address’ forged to display a Plesk domain could pass DKIM and DMARC validation and were not filtered. New domains now have the “Use DKIM spam protection system to sign outgoing email messages” option selected by default.
  
  Note: This improvement works only for new domains that have their DNS and mail hosting in Plesk.
• New domains now use the DMARC quarantine policy by default. This improvement protects outgoing mail against email spoofing.
  
  The DMARC policy defines how the receiver should treat email messages depending on the results of DKIM and SPF checks. The new default DMARC policy (v=DMARC1; adkim=s; aspf=s; p=quarantine) strictly enables DKIM and SPF checks. Emails that do not pass these checks are now put in quarantine (moved to the spam folder or flagged as suspicious).
  
  Note: This improvement works only for new domains that have their DNS and mail hosting in Plesk