Mission Impossible: Getting Legitimate email to Hotmail

Update: see part II

If you need to send mail to hotmail, add a month onto your delivery schedule (at least). During testing, mail from our domain was being marked as spam by Yahoo, Google and Hotmail.

Google, and Yahoo have straightforward processes for proving you're sending legitimate mail. Microsoft have SmartScreen.

Your IP(s) are being filtered based on the recommendations of the SmartScreen filter. SmartScreen is the spam filtering technology developed and operated by Microsoft. SmartScreen is built around the technology of machine learning. SmartScreen’s filters are trained to recognize what is spam and what isn’t spam. In short, we filter incoming emails that look like spam. I am not able to go into any specific details about what these filters specifically entail, as this would render them useless.

The above is a response to a support request to Microsoft I sent one month ago.

SmartScreen is so intelligent rather than placing the mail in a spam/junk folder for the user to decide, it makes the decision for them. It drops the email completely - obviously being so Smart it takes this unilateral decision because Hotmail users can't be trusted.

Microsoft go on to make some standard recommendations, most of which I was following, some of which I added.

Dedicated IP - Sending mail from dedicated IP addresses is better. This ensures the mail can be traced back.
Reverse DNS - Some spam filters check the reverse dns lookup matches the domain the mail claims to be from.
Valid SPF record - SPF sets a text record in DNS stating what servers are allowed send mail on behalf of this domain. Microsoft call this SenderID, not sure why because it looks and acts like SPF. Most spam filters check the SPF automatically by doing a DNS lookup on receipt of mail, but Microsoft insist that you register your domain with their SenderID program.

While you already have SPF/SenderID records, it did not appear that your domain was added to the SenderID program. We have added your domain to the SenderID program. This may take up to 2 business days to fully reflect in our systems. If you have any questions regarding this please let me know.

Again this isn't very smart.
Use Domainkeys - DomainKeys uses PKI to sign all mails from a domain. The idea is that to have a valid signature the mail *must* of come from a legitimate mail server with access to the domains private key. The public key is distributed using DNS.
Smart Network Data Services (SNDS) - This is a Microsoft service to track emails to Hotmail from your IPs. The concept is that any spam mail from your IPs can be caught. What I have established is that there have been no spam mails from my IP addresses, obviously SmartScreen is far too smart, so doesn't need to check.
Junk mail reporting program (JMRP) - Hotmail customers can report the mail from your domain as spam, which in turn is sent back to you after registering with this program. Give yourself plenty of time for this as 3 weeks after signing up I'm still waiting for my registration.
Privacy Policy + Terms and Conditions - I shared these with Microsoft to reassure them.

A month after this process started, and after several new support requests (follow ups to original requests went ignored) human intervention took place.

We have taken steps to implement a temporary mitigation to your mail delivery problem. During this period your emails should not experience any issues arriving at Hotmail. This period will also give our filters sufficient time to learn enough about your mailing practices such that after the mitigation expires your traffic will continue to arrive at Hotmail.

The conclusion? SmartScreen needs spoon feeding!