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I just recently setup an email auto-responder with a custom email server (in Java) and I will say it was a goddamn PITA. I did use the cited article and also this one is good: http://rimuhosting.com/support/settingupemail.jsp?mta=postfi...

Some things that are rather important:

1. Name your email server with "mail" some where in the name. Seriously don't call your email server crapbox.snaphop.com :)

2. Although you can send email as a relay on many different ports (2525, 8025, 587 (ssl)) you can really only receive on port 25.

3. You better have a PTR / reverse dns setup.

4. It takes at least a couple of hours before email servers will acknowledge you.

5. You can get away with out a SPF for a little bit but you really need if your going to blast a crap load of emails. Use this to test: http://www.kitterman.com/spf/validate.html



A couple of more gottchas are:

6. Some (most?) hosting providers are black listed and getting other email systems to recognize you as a valid agent is getting tougher and tougher.

7. You have to provide your own fail-over, or purchase it from someone else.


8. domain keys (DKIM) ?

did this recently on EC2 and found these helpful

http://pauldowman.com/2008/02/17/smtp-mail-from-ec2-web-serv...

http://www.practicalclouds.com/content/guide/sending-email-e...

DKIM on Ubuntu - https://help.ubuntu.com/community/Postfix/DKIM

Microsoft SPF record creation wizard - http://www.microsoft.com/mscorp/safety/content/technologies/...

not sending that much mail, but noticed after setting up SPF/DKIM/reverse DNS that the mail I sent to myself didn't end up in spam folders at gmail and hotmail etc., without having to send via a service like authsmtp.com.


If you can live with delayed messages there is not really a need for fail-over as most server will retry multiple times (default iirc multiple days). But you should have at least another email address available for example to communicate with your provider.




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