So firstly thank you to the ones that helped us. Our email error issue has now not coming up anymore. This is our situation:
So all has been setup wonderfully on our dedicated server - we aren't blacklisted and currently we send a few emails per hour. HOWEVER, alot of our emails WE send out are going to recipient spam boxes. How can we reduce this and is there any emailing software you can recommend that will help us send out better / more efficiently?
Do you know the recipient's email service? The reason I ask is that I recently worked with AOL because many of the AOL email addresses either blocked or quarantined email from my server. They removed their blacklist of the server, and invited me to be in their feedback loop program.
So far, I have had one email sent to me that they found suspicious. In one of my forums, I send the message from my forum software on the server, but the "reply-to" email address is my Google email address. Changing that "reply-to" header to reflect an email address at the same domain, complete with SPF and domain keys records, worked.
You might try sending one of the emails to another account on the same server or another one running SpamAssassin and see if there's anything in the headers that might be triggering a filter. If you don't have another account, send it to me ... frank AT messing-about.com ... and I'll see if there's anything I recognize. With your permission, I could even post the headers here the crowd-sourcing the solution.
The hotmail postmaster controls all accepted emails, they'll give you some info about exactly what they don't like about your server.
Makes no difference if its a dedicated or not, the postmaster controls received mail, a benefit of being the biggest mail server in the world is you can control who sends mail to your users.
A mail reputation is like a credit score, it starts off low and bad, hotmail yahoo are wary of new IP's and you have to prove to providers that your clean, they don't give the benefit of the doubt.
Reputation of your network as a whole also can have an effect.