emails going to spam

Does anyone else have this problem where mails generated by mailroom go to spam in gmail?

After seeing all my emails from mailroom go to spam in my gmail, I looked at the headers and have a pretty good guess as to why:

Received: from localhost.localdomain (localhost.localdomain [127.0.0.1]) by hub.sproutit.com (Postfix) with ESMTP id E986A1425FD

That looks about like the mail headers coming from my local postfix when developing on my powerbook. As far as a network like google is concerned, it may well look like any spammer on his pc relaying through your server.

Here are some headers that don’t go to spam:

Received: from dm51.mta.everyone.net (bigiplb-dsnat [172.16.0.19]) by omta18.mta.everyone.net (Postfix) with ESMTP id 5C70140CD6

or even

Received: from localhost (localhost.simplicato.com [127.0.0.1]) by host60a.simplicato.com (Postfix) with ESMTP id 3090C1095316

Those are 2 more web apps that are relaying through postfix. The first is a competitor of mailroom, the second is a web app of mine. All 3 use postfix, 2 use outsourced mail relays, only 1 goes to spam.

I am aware to the possibility that I may be on the wrong track as to why these emails from mailroom go to my spam. But after doing quick checks like reverse dns, those headers remain my best guess. They look unintentional.

The only reason I am taking the time to offer constructive criticism is because I’d like to have mailroom as an option.

If anyone with the same issue has some mailroom setup tips that resolve it, please let me know.

Hi Winston,

I’m sorry it took some time to respond to you; we were away for the holidays when you first wrote in.

I just want to clarify your problem here: are you saying all email sent by you from Mailroom to a Gmail account is ending up in spam or that email sent to Mailroom is put into spam by Mailroom?

Thanks,
-Charles