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Issue Mail send from webmail (Roundcube) goes to spam/junk

N

Nunile

New Pleskian
Hi all,

To begin, i'm a total newb trying to learn how to host a website and mailing. I have a technical background so I learn quick.
My problem: When I use Plesk webmail (Roundcube) to send a mail to [email protected], it goes to spam/junk.
When I send a mail to [email protected] it does not.

I'll try to explain my setup/configuration as detailled as possible

1. My domain is registered at GoDaddy
2. My DNS is managed at Cloudflare (use Cloudflare NS)
3. I Created a SSL/TLS certificate on Cloudflare, and imported it in Plesk
4. I run a Vultr VPS and installed Plesk on it
5. On this plesk I installed Wordpress (which works, the website part works)
6. On this plesk I use webmail (Roundcube), here is the problem.

After reading many, many articles and forums without coming to a solution, I am now typing this message.

Vultr IP adress : 11.22.33.444
Domain name : example.com

Other details
- In Vultr I setup a reverse DNS to: example.com


Since i'm new to all of this, i'm starting to lose a grip on how this all works.

Am i forgetting something here, any help is highly appreciated!
 
Last edited:
Sorry, I didn't notice you already set your reverse DNS. However it seems you've pointed your rDNS to the domain of your website. You'll need to point it to the host name of your server.

Have you set a custom host name for your server? If not, that would be you're first step. You can set your servers host name in Plesk at Tools & Settings > Server Settings. Then create a DNS record for your host name. And after that point the rDNS to your host name.
 
Thank you,

I changed my hostname of my server to: server.example.com
I changed the vultr reverse dns to : server.example.com
I created an A record to point server.example.com to 11.22.33.444

I am now waiting for them to propagate, i'll let you know if it worked
 
Last edited:
Good to hear you've been able solve the issues.

Unfortunately email can often be a b*tch to get working right for your server. Even if you have configured DKIM, SPF, rDNS, ect. As you have now experienced yourself. It is hard to tell why exactly your mail ends up in the Hotmail/Outlook spam folder. It could very well be that your IP is just black listed by Outlook/Microsoft. In that case there is now way to know for sure unfortunately.

Are your email messages being delivered to Gmail without issues?

I would recommend to configure IPv6 addresses for your server and domain. In my experience this can help the delivery of email message. There is certainly no guarantee it solves your issues. But it might still be worth a try.
 
I listed the domain using Microsoft Smart Network Data Service
My IP has a 'normal' status, which is good I think?


I installed the SSL certificate from Cloudflare on my Plesk Server:

Email still goes in spam
 
Last edited:
Nunile said:
@Rasp :
I installed the SSL certificate from Cloudflare on my Plesk Server:

Email still goes in spam
Click to expand...

I suspect the Cloudflare SSL certificate creates an conflict in your case. The Cloudflare SSL certificate is only ment for the encryption of connection between your server and Cloudflare. It is not a valid/accepted certificate for other type of connections. Hence the error on //email/testTo:.

I think (not 100% sure) that your solution would be to use an other (valid) certificate for your mail (and webmail and also for accessing Plesk). You could install the Let's Encrypt extension in Plesk (if you haven't already). And then install a Let's Encrypt certificate for webmail.novali.nl and mail.novali.nl. After which you can select the certificate in the Mail Settings of your domain in Plesk (as shown in your last screen shot).
 
Thank you, this solved the error thrown by //email/testTo:

However, mails are still flagged as junk/spam.

As far as I can see from many tests and checks, everything is correct:

CheckTLS.com -> Score: 100

MX Deliverability -> Score: 100

Mail-tester.com -> Score: 10/10

Reverse DNS check: OK

My IP is not on internal Outlook blacklist


Really don't know what to do next
 
Last edited:
If your mails only go into the junk folder when they are sent through webmail, the issue is caused by a mismatch of the submitting host name and your real host name. When webmail sends an email, this is sent from 127.0.0.1, which resolves to the name "localhost". The receiver resolves the name of the machine from where the connection is made and sees its host name. But it also resolves the name of the sender, which is different - "localhost". This difference lets the receiver think that the sender is spoofing.

To solve this issue, you need to tweak the Postfix configuration as follows:

Edit /etc/postfix/main.cf and search for the line that configures the
$myhostname
parameter. It is a comment by default. Remove the comment tag and set $myhostname to the host name of the system. That is the same domain name that you use when you open the Plesk panel and where the IP address of your public server IP resolves to; the general host name of the machine. It is not the domain name that is used in a specific subscription, but the server's name.

Save the file and restart Postfix
# service postfix restart

Then try to send from webmail again.
 
Dear Peter,

I also tried sending from Thunderbird (not webmail) using mail.novali.nl, this also went to SPAM. I contacted Microsoft Deliverability Support and they told me this:

"Recent activity coming from your IP (11.22.33.444) has been flagged by our system as suspicious, causing your IP to become blocked. I have conducted an investigation into the emails originating from your IP space and have implemented mitigation for your deliverability problem. This process may take 24 - 48 hours to replicate completely throughout our system."

I will now wait for 48 hours, and after try sending an email from my webmail client to see if it has worked.

If it did not work, I will try your changes to Postfix.

A big thank you to all forum members that have been supporting this thread! Really great :)
 
Last edited:
Nunile said:
Dear Peter,

I also tried sending from Thunderbird (not webmail) using mail.novali.nl, this also went to SPAM. I contacted Microsoft Deliverability Support and they told me this:

"Recent activity coming from your IP (11.22.33.444) has been flagged by our system as suspicious, causing your IP to become blocked. I have conducted an investigation into the emails originating from your IP space and have implemented mitigation for your deliverability problem. This process may take 24 - 48 hours to replicate completely throughout our system."

I will now wait for 48 hours, and after try sending an email from my webmail client to see if it has worked.

If it did not work, I will try your changes to Postfix.

A big thank you to all forum members that have been supporting this thread! Really great :)
Click to expand...
Dear Nunile,



I have the same problem as you.

Have you solved this by any chance?



Could you give me some help? this mistake is driving me crazy ...
 
andrycarone said:
Dear Nunile,



I have the same problem as you.

Have you solved this by any chance?



Could you give me some help? this mistake is driving me crazy ...
Click to expand...
Hi AndryCarona,

I was indeed able to fix the issue and my mails are now being received in the 'normal' inbox instead of spam. What kind of setup/configuration are you running? I also found out that the mails you sent to test it actually have to be mails like you would normally sent. If i send a mail with only 1 word in subject and 1 word as content it is still flagged as spam.
 
Nunile said:
Hi AndryCarona,

I was indeed able to fix the issue and my mails are now being received in the 'normal' inbox instead of spam. What kind of setup/configuration are you running? I also found out that the mails you sent to test it actually have to be mails like you would normally sent. If i send a mail with only 1 word in subject and 1 word as content it is still flagged as spam.
Click to expand...
Hi Nunile,

I have a VPS, within this with 20 domains.
For all these domains I have the webmail version with the roundcube service.

What happens to me, sending to outlook returns me in spam.
I'm trying them all,

At the moment my configuration is the following within plesk

Send from the specified IP addresses
selected IPv4 my platform ip address.
107.XXX.XX.XX

Inside plesk in dns setting I set:
PTR mail.domainname.it
Dmarc with forwarding to the email [email protected]
text: v = spf1 + a + mx + a: (name domainexample) -all
and then all the parameters given by default by plesk.


Then inside the Registrar Go daddy, I implemented all these dns:
@ / IP / A
webmail / IP / A
mail / IP / A
@ / mail.namedomain.it / MX
@ / v = spf1 etc etc + a: namedomain (as reported in plesk)
_Dmarc / [email protected] / txt
_smtp _tcp / x x xxx (standard plesk)



I am melted
:eek:
 
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