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I have Postfix with spamassassin and forward the emails (including spam) to gmail.com, my problem is that when I send "legitimate" emails to gmail.com it is marked as spam, I've done everything that the guidelines said like signing with DKIM, setup a SPF for my domains, require authentication for outbound mails, etc.

Now I wonder what I'm doing wrong?

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If you're using Google Apps email for your domain you can add your mail server to a whitelist in your admin interface. If you're just using plain old Gmail then you don't have that option. –  Ladadadada Dec 5 '11 at 23:06

2 Answers 2

If yours is

  1. A normal domain,
  2. It receives SPAM as well as normal emails, and
  3. You forward them to Gmail

your IP reputation may go down only when your SPAM emails outnumber genuine emails by a whole lot.

For example, many ISP's send email to GMail and some of them are SPAM and some of them normal emails. If Gmail were to determine reputation based only on IP's, most ISP's would have their mails going to SPAM folder.

I would suggest the following:

  1. Take this Email Server test and see if you have missed out on anything.
  2. If that still does not fix the issue, try to get a SMTP Service provider (at least temporarily) and direct emails through that provider. See if that improves delivery. If it does improve delivery, then the issue might be to do with your IP.
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What you're doing wrong is sending spam to gmail. It will detect that, and give your mail server a bad reputation in it's database, which then taints all the legitimate mail that comes from your server. Filter out the spam before forwarding it, or reconfigure your domain to send the mail directly to gmail.

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