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The email to AOL and the EMAIL to Port 25 - The DKIM signing process is different. When you send to AOL you're signing it with c=relaxed/simple when you send it to port 25 it's c=relaxed/relaxed. You're not really comparing apples to apples. With that being said, many DKIM validators have trouble with Simple conancalization, stick with relaxed. If you ...


Untrusted TLS connection established to I think you have a certificate chain error here. Make sure you are sending the intermediate certificate along with your certificate.


@Stefan You seem very knowledgeable which is awesome, I looked over your headers, without your domain name it makes it very hard to help troubleshoot. The one thing I did notice in your headers is that you're using "Simple/Simple" to sign your DKIM, you should really switch that over to "Relaxed/Relaxed". A lot of mail servers have trouble with simple. ...


One thing missing in the above (excellent) replies is to set up outbound TLS. Gmail has started to punish senders not using TLS, and other providers aren't saying anything but I'm sure they will follow suit.


There should be no issues becoming a small mail provider. You seem to be doing the right things. Many large providers don't get things right, and hopefully get most of their mail delivered. If mail is being sent to the SPAM folder, it is likely you have missed something. There should be a record of why you have delivery issues: For bounced messages ...


Nowadays, the spam activities is a real headache. The Big guys like Gmail, Microsoft, Yahoo etc. trying to secure their users from the spams. Hence, they must improve their techniques to filter the spams. And due to the secure reason, they could not disclose their policies. Hence, we could not configure our servers which can communicate their servers. ...

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