Are Hotmail cutting their own throat
Hotmail says I send Spam
Spam is a big problem for everyone. Postini estimate that spam now accounts for approximately 87% of all email on the Internet. There are several technologies that greatly reduce its penetration though, especially when used in combination. The exact technologies used by Hotmail are not clear, but if you’re having problems sending to Hotmail it might be worth having a look through their various FAQ’s, guidelines, anti-spam policies, and services aimed towards the sender. If you wade through all this and are confident your environment checks out but are still having no success sending to Hotmail, you can always contact their support staff, which is exactly what I did.
The response I got from Hotmail support was that their SmartScreen technology had identified email coming from my domain as being spam and had blocked my email server IP. Now, even if I was sending spam, somehow blacklisting the IP regardless of what other domains are sending email through that server does not seem especially “smart” to me. Hotmail support would not tell me why my domain was being flagged for spam, and when asked what the possible solutions were I was told I could sign up for 3rd party accreditation through Sender Score Certified (at a cost of $400USD start up, and $1000USD each year) who maintain the only whitelist service Hotmail use, and was also advised I could try tightening my SPF policy. Just to be especially vague the footer on the email also stated that there were no guarantees that any of the solutions offered would work. Great! So I could end up paying $1400USD to be accredited by a 3rd party whitelist just so I can send to Hotmail, and there is still no guarantee that if I get accreditation that my mail will get through.
I took the other option and tightened my SPF policy so that it explicitly stated what servers were able to send email on behalf of my domain using the “-all” option. I waited 72 hours as the hotmail support said it would take to update Hotmail’s various caches, but still I could not send emails to Hotmail. I then came across this article on openspf which pointed out that in fact the SenderID technology which Microsoft had championed (and Hotmail use) as another anti spam technology was in fact highly incompatible with SPF policies. Microsoft were apparently even made aware of this prior to the final release, but did not do anything to correct it despite there being hundreds of thousands of domains with active SPF policies in effect at the time. I updated my domain with a SenderID policy and waited another 72 hours but still the problem persisted. I contacted hotmail support again who informed me that if SmartScreen was flagging my email server IP due to a reputation issue (or lack of it) then it might take longer than 72 hours for the problem to rectify itself.