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I have a server on which I host multiple domains. I recently installed a redmine installation underneath one of those domains. I set up the installation to send e-mails through sendmail. The e-mails are being sent, however, when they arrive in my gmail account, many of them are going straight to spam. I'm trying to lessen that likelihood. I noticed that they are described as being from "no-reply@my-domain.net" via "my-other-domain.com" where the second one is the domain for another site I have set up on this machine, and also happens to be the one listed in the /etc/hosts file. How can I remove that via portion? Also, does it affect the likelihood of my e-mail being judged as spam?

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Have you configured reverse DNS? –  Lucas Kauffman Mar 15 '12 at 15:14
    
Probably not, the only configuration I've done is of apache2. Actually, now that I think about it. I think I did, a long time ago. The sort of thing you do once and then forget about. I've added domains since then. But I just realized that for one of the oldest domains, it isn't adding the 'via' part. –  Daniel Bingham Mar 15 '12 at 15:17
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Aha, that might be the culprit, several mail services categorize mail as spam when no reverse dns is configured. Especially gmail. –  Lucas Kauffman Mar 15 '12 at 15:52
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