Outgoing mail blocked as spam at receiving server

[techhelp]

I feel so dumb on this issue. I don't know what to search the forums for so I am sorry if this has been dealt with before.
This is my first Zimbra server and I truly love what I see, in fact, I stopped learning EX2010 as my first shift from Hmail. Don't laugh please.

The install has gone remarkably well, although I built/killed/built the box before I started to use it so that I could document my methods just in case.

Now I don't want to re-build the server for this issue if at all possible.
1. I setup the server as webmail.original.domain.here
2. I then setup the domain original.domain.here (might have done this incorrectly)
3. After setting up the mx record for original.domain.here I was happy with what happened and decided to create
4. new.domain.here
5. configured the server to be a secondary mail server so as to start using new.domain.here in a split dns and it seems to be working by collecting POP mail from the primary ISP server.

The Issue I have is that mail sent from new.domain.here through the ISP server as smart host, is being junk mailed at some locations. I determined that mail sent from me@new.domain.here is showing as originating from original.domain.here and being blocked or treated as bulk mail.

So again, I am sorry if I am asking a question that has been dealt with, or if this is a silly issue, but I am curious if this is an issue of the canonical name or if I need to setup a masquerade/alias of the domain names.

I don't want to rebuild as know I eventually would like to host a few domain names on this box. Would it be better to simply setup mx records for new.domain.here, although I suspect the sending will still be the same.

Or, would it be better to drop the smart host and do a direct send from each of the domains.

Thoughts are appreciated.

[phoenix]

Originally Posted by techhelp

Or, would it be better to drop the smart host and do a direct send from each of the domains.

Unless your ISP blocks port 25 for outbound email there's no reason why you shouldn't send mail directly, unless..... Do you have a dynamic IP address and do you have a reverse DNS for your IP, if you don't have both of those you may (probably will with some mail servers) encounter problems. Are you any block lists? Do you have any idea why the receiving mail servers think your mail is spam? You need to find that out from them.

[techhelp]

As stated previously, the Zimbra server was setup with one initial domain as "original.domain.name" and an MX record and DNS are correct for that. No apparent issues.

The blocks happen from mail sent to some servers, from the newly added domain "new.domain.name" that I wish to host on the same server. Looking at the mail headers, and an explanation from the receiving party, is that the mail arrives as if it was sent from "original.domain.name" and they blocked it as bulk mail.

I am led to believe that I should be getting my ISP, who is also our smart host, to configure a reverse DNS record for the domain. For the second domain I am polling pop3 mail from them, and sending out through them until such time as I have finished testing the server and migrated all users over. At that time I MAY point get the ISP to change the MX record to point to our IP (static btw).

I was hoping to keep the ISP as the primary server to keep collecting mail in the event we are offline for some reason... and it buys me time to test and get a secondary server online.

I am more curious as to if it is possible to change the headers to show that is it coming from "new.domain.name" rather than "original.domain.name"... or if this is not even a necessary issue to deal with.

I am new-ish to this as under Hmail *cough* I did not seem to have this issue, or I never found out about it.

Thanks for your reply.

[phoenix]

Originally Posted by techhelp

As stated previously, the Zimbra server was setup with one initial domain as "original.domain.name" and an MX record and DNS are correct for that. No apparent issues.

The blocks happen from mail sent to some servers, from the newly added domain "new.domain.name" that I wish to host on the same server. Looking at the mail headers, and an explanation from the receiving party, is that the mail arrives as if it was sent from "original.domain.name" and they blocked it as bulk mail.

Why aren't you using the correct domain name format of domain1.com, domain2.com etc.. - by using 'original.domain.name' what you've set-up is a sub-domain not a domain.

Originally Posted by techhelp

I am led to believe that I should be getting my ISP, who is also our smart host, to configure a reverse DNS record for the domain.

That would be correct, the ISP is the one that creates a reverse DNS.

Originally Posted by techhelp

I was hoping to keep the ISP as the primary server to keep collecting mail in the event we are offline for some reason... and it buys me time to test and get a secondary server online.

I think a better solution for that would be to have your external DNS records hosted by a company that provides a Backup MX for your domain(s), I use EasyDNS.com for and they provide that service. The mail is held for up-to five days and then forwarded to your server when it's back on-line plus they look after the spam problem. I don't consider ISPs to be the best choice as your backup mail server, they can be notoriously unreliable (I'm not saying your ISP is) and your more likely to get a better service from a company that specialises in those functions.

Originally Posted by techhelp

I am more curious as to if it is possible to change the headers to show that is it coming from "new.domain.name" rather than "original.domain.name"... or if this is not even a necessary issue to deal with.

You shouldn't be seeing any such problem at the receiving servers, you should be able to host multiple domains and send to any user without problems - I do exactly that on my own server. Do you actually mean that the email is showing the Received header as coming the server and it has the FQDN of that server?

[techhelp]

My ISP may be able to provide the backup MX. They suggested being able to filter virus/spam and then forward, I understood this feature as being a catchall and having to poll this via POP3. Will check on Monday if it is a true backup MX.

I have already asked my ISP to setup DNS reverse lookup... I hope they understand the request. They could not figure out permissions on their web server to allow a cgi script to run... so that is my next project for Zimbra. Write a Zimlet to provide an iframe inclusion of a cgi script for an in/out board... and have my Zimbra server host that small script. I fear I am jumping in too fast, but I do not want to even consider going back to the M$ product.

To clarify:
I built the server and the FQDN is webmail.domain1.com. I setup an MX record to reflect that fact.
The initial admin account was admin@webmail.domain1.com
I did not want to create accounts @webmail.domain1.com so I created @domain1.com. When mail flow was working and I felt comfortable with Zimbra, I setup another domain2.com on the same server. I wish to keep both unique domains on this server, however only domain2.com will receive mail from my ISP.

As it appears I was not using understandable naming conventions, perhaps this will be of better value.


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Date: Tue, 16 Mar 2010 16:56:25 -0500 (CDT)
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