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I have setup a new Zimbra Open Source installation. This is a new email server and the IP of this server is not Black listed in most prominent Block Lists. But what ever I have tried the emails still end up in the Spam folder. The headers which I received in my gmail account is as given is as below

http://pastie.org/1308039

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Full marks for providing relevant information in the question! Its the nature of spam detection that most companies are cagey about publishing information about how they detect spam - and in the case of bayesian filtering they may not even know! Have you tried the Gmail bulk sender guidelines? mail.google.com/support/bin/answer.py?answer=17205 – symcbean Nov 18 '10 at 14:40
    
Yup tried that. But no hope. – user60699 Nov 18 '10 at 15:14
    
how do you manage the MX registration. Are you using a fqdn (best practice) or the ip for the MX tag (not recommended). Do you have the PTR correctly declared on your public ip? Is a new domain or you was migrate from another server. Some times change the MX direction reduce the "reputation" of your domain. Check the Gmail bulk sender guidelines too. – Carlos Mario Mora Restrepo May 26 at 0:44

You know getting mail to Yahoo, Hotmail and Gmail can be a real hassle. There are lots of people using relays as smtp2go or amazon for getting their mail through. One catch that you maybe missed (although I didn't see it in the headers) could be disabling the Origin-IP header which exposes the ip address of the person composing the e-mail and could be used as an originating ip address. You can disable it by:

zmprov mcf zimbraSmtpSendAddOriginatingIP FALSE

If you give up and want to try an extra relay, you can find more on that in this thread:

Using Amazon SES to send mails to specific domains in Zimbra

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