Email sent from board classified as spam

I have a new board setup and users are saying that they are not getting registration email, new message emails, post reply emails, etc., I asked them to check their spam filters and sure enough they are there. I have followed all of the topics I could find here on things to look at, RDNS, smtp, enabling - f parameter, etc. and nothing seems to help.

My domain is less than a month old. The site runs on a VPS with a private IP. I have ran the domain and IP through various spam checkers and everything checks out ok.

I ran some tests myself, and when they go to my spam folder in gmail, google says the reason is: "It's similar to messages that were detected by our spam filters"

I looked up more info on this and found:

These two messages indicate that you’ve got a content problem.

  • Why is this message in Spam? It’s similar to messages that were detected by our spam filters.
  • Why is this message in Spam? It contains content that’s typically used in spam messages.
Your content has problems. It’s been judged not valuable or contains content that is such a hard sell that it triggers Google’s content-based filters. Things like all-image emails or overuse of sales promotional words and phrases are to blame here, so make sure there’s legitimate editorial content in your messages to balance out the sales pitches. Bottom line: send more valuable email, email that people actually want, and they’ll stop flagging it as spam. Make sure you have prominent unsubscribe links and use the List-Unsubscribe header option if your email service provider offers it so that people who don’t want to be on your list can leave instead of flagging you as spam.

I have some other forums running vBulletin & MyBB and have never had this problem.

Not sure what to do.

Any help would be greatly appreciated
 
I did with Hotmail and Google. Once I enabled RDNS, DKIM signing and SPF the Google problem pretty much resolved itself. Hotmail on the other hand - some of them never even showed up. I ended up having to contact MS about it and after they checked to make sure my /24 was clean and that the messages WERE being signed correctly and met their other requirements were supposed to make a "temporary exception" until my domains history is lengthier (pure MS gobbledy-gook). I haven't checked again (have to create yet another junk hotmail account) to see if it has been done.
 
Thanks for the reply. I have done RDNS and DKIM, but not sure about SPF. I'm checking with my host now. I'm wondering if having a new domain largely plays into this?

I did with Hotmail and Google. Once I enabled RDNS, DKIM signing and SPF the Google problem pretty much resolved itself. Hotmail on the other hand - some of them never even showed up. I ended up having to contact MS about it and after they checked to make sure my /24 was clean and that the messages WERE being signed correctly and met their other requirements were supposed to make a "temporary exception" until my domains history is lengthier (pure MS gobbledy-gook). I haven't checked again (have to create yet another junk hotmail account) to see if it has been done.
 
Thanks for the reply. I have done RDNS and DKIM, but not sure about SPF. I'm checking with my host now. I'm wondering if having a new domain largely plays into this?
That's what MS's email indicated. You have to develop a reputation - which plays into their filtering.
 
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