Selfhosting email, and sending email to Microsoft.

About once a year one of my outgoing email servers will magically pop up on Microsofts blacklist of email servers. The exact status in SNDS is “Blocked due to user complaints or other evidence of spamming“, which is a bit ironic since the weekly volume of emails that go to Microsoft controlled domains seldom is higher than 5 and they are all personal emails.
The error message the MTA recieves is “550 5.7.1 Unfortunately, messages from [xxx.xxx.xxx.xxx] weren’t sent. Please contact your Internet service provider since part of their network is on our block list (S3140). You can also refer your provider to http://mail.live.com/mail/troubleshooting.aspx#errors.” in case anyone ends up here via google.

I’m not going to bitch and moan or attempt to guess why the server ends up on the list since it isn’t something I can influence
(just submit a support request and wait), instead I’ll post some tips and pointers to useful tools you should be using:

SPF – Sender Policy Framework
Specify which IPs are allowed too send mail for your domains, also determine what should happen with mail that is recieved from unauthorized IPs.

DKIM – DomainKeys Identified Mail
Outgoing mail servers for a domain can sign the emails and thereby allow recipients to verify that the email really came from a valid mail server and is not from a spoofed sender.

DMARC – Domain-based Message Authentication, Reporting & Conformance
DMARC allows you to specify policies for domains or subdomains in regards to “what should happen if an email fails DKIM or SPF” and where/if to send reports for Emails recieved by other mail servers.

SNDS – Smart Network Data Service
Allows you to monitor the IPs of your mailservers as viewed by the Outlook.com system.

JMRP – Junk Email Reporting Program
Forwards the full message with headers of any email marked as “junk” or “phishing” by Outlook.com users

MX Toolbox
MXtoolbox is a great website for testing your mail server settings, they also have a free_monitoring service for one IP, so you can get alerted if your IP shows up on a Blacklist.

Last but not least I use the following small script to monitor the status of my servers according to Microsoft. I call the script via a daily cronjob, and if a server is blacklisted, it sends an alert. Go to Automated Data Access first to generate an API key.

#!/usr/bin/env bash

sdns_key="&lt;&lt;insert API key here&gt;&gt;"
recipient="&lt;&lt;email to send alerts to&gt;&gt;"

if [[ "${sdns_key}" == '' ]]; then
        exit 0
fi

_URL_ip="https://sendersupport.olc.protection.outlook.com/snds/ipStatus.aspx?key=${sdns_key}"
_URL_data="https://sendersupport.olc.protection.outlook.com/snds/data.aspx?key=${sdns_key}"

content="$(curl -s "${_URL_ip}")"

if [[ ${#content} -gt 0 ]]; then
        {
        echo "${content}"
        echo
        curl -s "${_URL_data}"
    } | mailx -s "Microsoft SNDS status" ${recipient}
    exit 1
fi

#!/usr/bin/env bash

sdns_key="<<insert API key here>>"

recipient="<<email to send alerts to>>"

if [[ "${sdns_key}" == '' ]]; then

exit 0

_URL_ip="https://sendersupport.olc.protection.outlook.com/snds/ipStatus.aspx?key=${sdns_key}"

_URL_data="https://sendersupport.olc.protection.outlook.com/snds/data.aspx?key=${sdns_key}"

content="$(curl -s "${_URL_ip}")"

if [[ ${#content} -gt 0 ]]; then

{

echo "${content}"

echo

curl -s "${_URL_data}"

} | mailx -s "Microsoft SNDS status" ${recipient}

exit 1

And if all else fails and your IP does end up blacklisted in SNDS, you can go here to submit a ticket to get back off (although I’d suggest checking your mail server logs and the status of the IP on other RBLs first, just to make sure).

http://go.microsoft.com/fwlink/?LinkID=614866