imap e-mail is always sent as spam ?

AudiAddict

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I set-up a new domain for one of my family members and they tried to set it up in outlook 2010.

All e-mail sent from his computer is marked as SPAM. Even when sending it to another domain on the same directadmin server. See the message below:

Code:
Spam detection software, running on the system "webserver.mydomain.com", has identified this incoming email as possible spam.  The original message has been attached to this so you can view it (if it isn't spam) or label similar future email.  If you have any questions, see the administrator of that system for details.

Content preview:  Test! [...] 

Content analysis details:   (8.6 points, 7.5 required)

 pts rule name              description
---- ---------------------- --------------------------------------------------
 0.0 FSL_HELO_NON_FQDN_1    FSL_HELO_NON_FQDN_1
 3.3 RCVD_IN_PBL            RBL: Received via a relay in Spamhaus PBL
                            [76.115.166.144 listed in zen.spamhaus.org]
 0.7 SPF_SOFTFAIL           SPF: sender does not match SPF record (softfail)
 1.3 RCVD_IN_RP_RNBL        RBL: Relay in RNBL,
                            https://senderscore.org/blacklistlookup/
                           [76.115.166.144 listed in bl.score.senderscore.com]
 0.0 HTML_MESSAGE           BODY: HTML included in message
-0.5 BAYES_05               BODY: Bayes spam probability is 1 to 5%
                            [score: 0.0192]
 0.0 RCVD_IN_SORBS_DUL      RBL: SORBS: sent directly from dynamic IP address
                            [76.115.166.144 listed in dnsbl.sorbs.net]
 1.0 RDNS_DYNAMIC           Delivered to internal network by host with
                            dynamic-looking rDNS
 0.0 HELO_NO_DOMAIN         Relay reports its domain incorrectly
 0.0 DYN_RDNS_SHORT_HELO_HTML Sent by dynamic rDNS, short HELO, and HTML
 2.8 DOS_OUTLOOK_TO_MX      Delivered direct to MX with Outlook headers

The original message was not completely plain text, and may be unsafe to open with some email clients; in particular, it may contain a virus, or confirm that your address can receive spam.  If you wish to view it, it may be safer to save it to a file and open it with an editor.

Shouldn't he be able to use my own directadmin server as a SMTP server? so mail.hisdomain.com ? Why is it complaining that his dynamic ip causing the problem? Shouldn't it be sent and relayed by my directadmin ip (and not 76.115.166.144)?

I use my provider smtp server for my mail domains on this directadmin server so have never noticed this problem.

Here is a screenshot of the settings and the domain, please dont quote the domain name as it will appear in google results (just use a substitute.. thanks)
http://i.imgur.com/Og2Sb.png

Anybody know what's going on? It seems the problem only happends from his outlook client and not from the webmail (roundcube). Is there no other option but to use his own smtp server from his ISP?
 
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Hello,

IMAP has nothing to do with sending emails, this protocol is for reading messages in your box. Regarding your issue, you might need to whitelist his email and/or IP on your server.
 
Thanks for your reply, but can you please explain how sending mail with imap works then? SMTP?

Why would I need to whitelist a dynamic IP? He is using imap in outlook (see the link to the .png in the start post above with all the settings) and his mail is sent by his own pc and not rellayed with my own directadmin server?

Shouldn't he be able to use my own directadmin server as a SMTP server? so mail.hisdomain.com ? Why is it complaining that his dynamic ip causing the problem? Shouldn't it be sent and relayed by my directadmin ip (and not 76.115.166.144)?

Here is a screenshot of the settings and the domain, please dont quote the domain name as it will appear in google results (just use a substitute.. thanks)
http://i.imgur.com/Og2Sb.png

Anybody know what's going on? It seems the problem only happends from his outlook client and not from the webmail (roundcube). Is there no other option but to use his own smtp server from his ISP?

So he uses SMTP mail.mydomain.com and it's being sent by his local pc and thus being blocked as spam? Why is it not using my directadmin ip for sending?
When sends a mail through webmail it does not get blocked.
 
Cause webmail use server ip. Actually email should be sent via server ip, maybe he dont use authentication on smtp, or maybe your server refuse the connection cause of his ip.

Regards
 
He is able to send the mail using outlook, so my server probably doesn't refuse it then?

He don't use authentication on smtp? Does he need to configure that in outlook? Doesn;'t sound very user/newbie friendly (or does outlook detect this?), and I'm not sure if I have that enabled server side?

What I don't understand is that you enter a smtp server in outlook and it's not using/relaying it through that server? Or am I wrong? see the topic start for the error code and the link to the settings (screenshot)
 
Authentication would be suggested for dont be an open relay and for security reason.

In outlook 2010 can be set in "advance section" on email configuration page.

Also, maybe he got a virus or spyware, also, without domain name we cannot define if he is using correct smtp server or even if dns are correct.

I would you suggest to use SpamBlocker 4.1 (find in this forum) for improove security of your smtp server (and put authentication as a must)

Regards
 
Check my topic start, there is a link to my mail settings for troubleshooting. I used a link because I rather not have it come in google results.

My security is fine, this is a client side issue related to SMTP and other mailservers complaining that SPF/Reverse dns is wrong and that the ip is dynamic and not static (thus causing the block at spamhause.org).
This is all NORMAL because mail is sent by his local outlook client and for some reason it's not using the smtp server that he configured. That I don't understand.

I can reproduce the problem with my own outlook and another domain. It seems to be a directadmin / outlook issue.
 
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As i sayd, try to set authentication for smtp server, i did see on the screenshot, just click on "more settings" button and go to smtp authentication settings.

Regards
 
I did that, it works, but still sent and received by local ip and not the SMTP mail server and causing it to be SPAM.
 
mmmh, have you tryed to send to an external server instead on a domain on same server?

Can you try send me an email for check which ip is coming?

Regards
 
Doing a lookup on the mail.* server you have in your image, I see it resolves to a homeunix.net domain. That is one of the dyndns.com which leads me to believe that the mailserver that is configured is a dynamic IP address and therefore not really good to use for sending email. What id was this:
nslookup mail.yourdomain.com
Which returned a homeunix.net domain name and an IP address. I then did an nslookup on the IP address (checking for reverse DNS) and it came back empty. Based on this, I would say it is reporting this correctly. First don't ever run a mail server on a dynamic IP, too many other servers will refuse email from it. If that is not your mailserver then perhaps that user hasn't updated his domain's DNS entries to use your server.
 
I may have missed something but for DirectAdmin to accept email from a dynamic IP# and not see it as spam, it should be submitted from his local machine to port 587 on the server, not port 25.

Jeff
 
Thanks for your reply, but can you please explain how sending mail with imap works then? SMTP?

Yes, emails are being sent through SMTP.

Why would I need to whitelist a dynamic IP?

Because it's blacklisted, see

RBL: Received via a relay in Spamhaus PBL [76.115.166.144 listed in zen.spamhaus.org]

If the IP changes every time. then you might need to add email into whitelist of SpamAssassin.
 
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