How to send mass emails legally through your own SMTP servers without being black listed?

Hello all,

Having 2 sendmail servers and a list of customers and partners, how can I fire personalized material to each customer or potential customer without being black listed by spam black lists?

In other words, if you have a specific marketing company how can I legally fire a bunch of emails from time to time?

I understand that you can hire companies for that. If they can legally do it, what is the legal procedure to atain the same functionality?

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Check out this thread I answered the other day, and let me know if you have any further questions/concerns.
CarlosScheideckerAuthor Commented:

Thanks. I have not found that question before. I wonder what do you do if you get flagged as spam. Emails we will be sending are unique per user and there is an option to unsubscribe. The contents are also clean marketing contents which is also OK.

So, how do you flag yourself out and how long does that take just in case.

I am planning to use Sendmail as the SMTP servers and have a few of those, like 2 or 3 each with its unique IP and host name. Is that what you meant on that?

If you follow all of my instructions, you should not get flagged as spam.  Of course that all depends on the receiving servers policies, and if there is one thing that rings true in the mail world, it's that you can't fix all the stupid.  You could have 100% totally legit mails that nobody except for 1 company sends to the spam folder.  When that is the case, the only thing you can do is reach out to that company and setup some policies for your domain(s).

I am planning to use Sendmail as the SMTP servers and have a few of those, like 2 or 3 each with its unique IP and host name. Is that what you meant on that?

Can you be more specific about what you are referring to?  Happy to help.
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CarlosScheideckerAuthor Commented:

There will be 3 Linux box with sendmail. One is for our internal emails with imap and pop access. The other 2 are two sendmail boxes just to send emails.

Hence, on the DNS records shall I add those two boxes with less priority MX records too? What is the best trick on the DNS records for those?

You could do a few things, it all depends on how much complexity and admin overhead you want for your mail infrastructure.

1.  Keep MX record as-is with only the internal mail server, use marketing mailing servers for sending only.
2.  Add 2 marketing servers as backup MX's, and configure them to spool mails when primary MX is down
3.  Add 2 marketing servers as primary MX's with equal weight, which relay to the internal sendmail server where the mailboxes live.  Use internal server for sending "normal" mails only, and the other 2 sendmail servers sending only marketing.  imap/pop access is unchanged.

Personally I would do #3, but any of the options are valid.  Whichever you choose, make sure the SPF record has all the IP's you will be sending from for both internal and marketing mails.

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CarlosScheideckerAuthor Commented:

So on Sendmail I would then have to create only accounts on the main one, right? The other 2 which are marketing, have no accounts but an alias or virtualuser table to forward those. How can I make sure that emails will not be delivered to the other 2 servers other than the main internal one? The MX records can have their priorities chaged as to the number you assign to them. As for Sendmail only the internal would have dovecot service running as the other two are SMTP sendmail only. I wonder if you would have a sample of such configuration. Thanks.
I don't have a sample sendmail config off hand, but there is lots of info out there for what you need to do.

You need to add the 2 new boxes as equal priority MX records and remove any others.
Configure sendmail on those 2 boxes to relay all mail for your domain to the main sendmail server.  You can probably just configure sendmail on those boxes to deliver to a "Smart Host" which would be the internal machine.  No accounts or aliases or virtualusers should be needed, you will be strictly relaying mail to the final destination, nothing more.

So do some research on sendmail as a relay, and using smart hosts in sendmail, etc.  It's pretty straight forward and should only be a few config changes at most.  I would setup the internal server to only accept mail from the 2 new boxes, but that is up to you and can be done once you get overall delivery/sending working.
Once you start reading some links on what needs to be done, I can double check any config changes you plan on making if you want, but I think you will be able to figure it out yourself :)  Either way let me know how it works out or if you have any more questions.
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