Issue mail not received by google

[Epizefiri]

Server operating system version

Ubuntu 20.04.5 LTS

Plesk version and microupdate number

Plesk Obsidian 18.0.47

Hi there,
I'm running Plesk Obsidian 18.0.47 on Ubuntu 20.04.5 LTS.

A client of mine noticed that often his emails are signed as SPAM on gmail.

• We did a quick test with mail-tester and looks like our setting are perfect ( Spam Test Result )
• I tried to send an email from his account to a Gmail Account that never received email from my client, and the mail arrived normally

At this point we tried glockapps.com, that basically gives you a list of email address and ask you to send a test email to this addresses. With our surprise we've got this result


We tried the same test from another email address on the same plesk installation ( but with different domain ) and we've got the same result.

I don't know what to think about it, is the result of glockapps trustable? Am I in a gmail ban list? how do I get out of it?

 

[Olray]

Google requires you to implement both DMARC and DKIM nowadays:

Set up DKIM - Google Workspace Admin Help

Gmail users: If you’re getting spam or phishing messages in Gmail, go here instead. If you’re having trouble sending or receiving emails in Gma

support.google.com

The way I know Google, it's a simple market entry barrier to push small suppliers out of the market.

 

[Epizefiri]

Google requires you to implement both DMARC and DKIM nowadays:

Set up DKIM - Google Workspace Admin Help

Gmail users: If you’re getting spam or phishing messages in Gmail, go here instead. If you’re having trouble sending or receiving emails in Gma

support.google.com

The way I know Google, it's a simple market entry barrier to push small suppliers out of the market.

Hi Olray,
as you can see i have both DMARC and DKIM Spam Test Result

 

[WebHostingAce]

How do you send these emails? from the Webmail or from a Email Client?

Please send an Email to GMail. Then check the Email header.

SPF:
DKIM:
DMARC:

Do they all 'PASS'?

Also check the,

Received: from xxx.xxxx.tld (xxx.xxxx.tld. [IP])

Does this IP's rDNS match the sending host (xxx.xxxx.tld) ?

 

[WebHostingAce]

I can see your Spam Test Results. But it will be good to see how Gmail see these email by viewing the "Original Message"

Also your email footer (Link and Images) might be causing this issue as well. Is this a new server/domain?

There are many factors GMail look for before landing your email in the user's inbox.

 

[Epizefiri]

Hi,
this is an email that was in the spam folder of a Google Workplace account


SPF, DKIM and DMARC are all signed as "PASS".

The email have some images from the same domain of the email sender.
The server is one year old, the domain 2 years old, on this server since June.

This is the dump of the headers of the email Primo Modica, [5 dic 2022, 10:52:43]: Delivered-To: [email protected] Received:. - e5dfa1a0

I don't understand, everything looks correct

 

[Olray]

I suggest to create a Google Postmaster account to find out why your emails are blocked:

Sign in - Google Accounts

I didn't try but should it work as intended you will get a detailed report.

 

[Epizefiri]

Hi Olray,
thanks for your suggestion, but the Google Postmaster needs hundreds of emails to start log something.
I activated 3 days ago and it still shows me this warning

No data available. Please try again later.
Before Postmaster Tools can make the data in this chart visible, the domain must meet certain conditions. Please refer to the support page for further details.

 

[Olray]

You're not spamming enough

 

[Kaspar]

If I am not mistaken Postmaster needs thousands (if not millions) of monthly mails before it lists any data/information. Although on this page they mention "100 messages per day to unique Gmail users".

Google Postmaster Tools - What it's and how it can help you - Dynamics 365 Customer Insights

Learn how to use Google Postmaster Tools to gain delivery insights in Dynamics 365 Customer Insights - Journeys.

learn.microsoft.com

 

[Epizefiri]

No chances to do this numbers for my VPS.
What now?

 

[Olray]

Thanks Google, for another useless service. I have run out of ideas (didn't take too long, huh?)
Perhaps check out the headers of the few delivered e-mails to find out what to change to lower the overall spam score? Perhaps your mails are close to pass

 

[Kaspar]

Only Google knows what's causing the issues you're facing but since they're keeping it to themselves you have limited options I am afraid. Personally I would thoroughly test and troubleshoot your server setup. Setup a test server with the same provider with an identical configuration. See if that causes the same issues. If so, setup a test server with another provider. Rule out as many variables as you can. That's probably not a lot fun to do, but it might help you to find a setup that works.

Also, Google likes IPv6. Try configuring an IPv6 addresses to your server if you havent already.

Other things you can consider:

• Wait it out. See if things improve over time. Sometimes all thats needed is some patience.
• Get a new IP address for your server (if it's an VPS you might be able to clone it, otherwise you can maybe use a backup and restore it on a new server for migration). Not ideal, but worth considering. This is based on the assumption that your IP address might be contaminated. There is however no guarantee that another IP address solves your issue.
• Use an email provider (ESP) to route all email trough. This can be costly if you have high mail volume.

 

[Epizefiri]

Hi Kaspar,
thanks for your response, I can feel that you did as much as possible to be gentle to me.

I'll try the IPV6 switch, in '22 is probably time for this

I'm a bit worried about the change of IP, I've around 35 websites with different domains on this machine, some domains are own by my clients. I'd need a lot of work and time to change all the records :\

When you talk about ESP, you mean something like sendgrid? does it exist something that I can use as a proxy for the whole VPS without changing the settings of every email account (we are talking about 160 mail addresses)?

 

[Kaspar]

I'll try the IPV6 switch, in '22 is probably time for this

Almost '23 No guarantee this will solve anything for you, but worth having anyway.

I'm a bit worried about the change of IP, I've around 35 websites with different domains on this machine, some domains are own by my clients. I'd need a lot of work and time to change all the records :\

There is no guarantee a different IP will solve your issue. So before putting in a lot of work and effort setup a (test) server with a different IP to see if that bares any fruit.

does it exist something that I can use as a proxy for the whole VPS without changing the settings of every email account (we are talking about 160 mail addresses)?

Sure a proxy could work too. You can always consider setting up your own proxy.

When you talk about ESP, you mean something like sendgrid?

Yes. You just relay all (outgoing) email to sendgrid (or any other ESP) from your server. I don't think you need to change much settings for email accounts on your Plesk server. Likely only SPF and DKIM records in each domains DNS.

As an example this Plesk support article describes how to change postfix settings to relay all email to sendgrid.

https://support.plesk.com/hc/en-us/articles/115004060494

 

[mow]

This is the dump of the headers of the email Primo Modica, [5 dic 2022, 10:52:43]: Delivered-To: [email protected] Received:. - e5dfa1a0
I don't understand, everything looks correct

From: Le Fate Milano <[email protected]>
To: [email protected]
Subject: LE FATE MILANO - PROVA
Message-ID: <[email protected]

milano.it>
X-Sender: [email protected]
Organization: Le Fate Milano

Was the line break in the message ID already in the source?

Otherwise, an all-caps subject is a sure way to get caught in the spam filter.

 

[Epizefiri]

Was the line break in the message ID already in the source?

Otherwise, an all-caps subject is a sure way to get caught in the spam filter.

No, the line break is due to a copy and paste error

Otherwise, an all-caps subject is a sure way to get caught in the spam filter.

I got the same result with a no caps lock subject ( OUCH! )