TL;DR: IF YOU ARE STILL EXPERIENCING DELIVERABILITY ISSUES, CONTACT OUTLOOK.COM DELIVERABILITY SUPPORT: <http://go.microsoft.com/fwlink/?LinkID=614866>
I have contacted Outlook.com Deliverability Support and will report back to the list if the results from the interaction are of public interest. On 2018-01-06 02:19 AM, Peter <pe...@pajamian.dhs.org> wrote: > It's not the first time I've seen MS accused of dropping mail. Mine (first post in thread) were not accusations. They were corroborated test results. > I suggest you have a look at: > https://mail.live.com/mail/troubleshooting.aspx > [...] > If you're still having problems I would sign up for SNDS at: > https://postmaster.live.com/snds/index.aspx > > ...that will allow you to check your IP reputation with Microsoft, if > it's blocked you can contact support and they should remove the block. Thank you for the reminder. I was already registered for SNDS just did not remember. It is not exactly a popular destination. Everything normal there. I used the Troubleshooting page you linked and worked through it step by step, to no avail. All things were already implemented properly in the past. One thing I unearthed that was useful: IF YOU ARE STILL EXPERIENCING DELIVERABILITY ISSUES, CONTACT OUTLOOK.COM DELIVERABILITY SUPPORT: <http://go.microsoft.com/fwlink/?LinkID=614866> Things that I have done before contacting outlook.com deliverability support: (A) on my sender domain: * verified that my sender domain has correct SPF set-up <http://www.kitterman.com/spf/validate.html> * verified that my sender domain has correct DKIM set-up <https://protodave.com/tools/dkim-key-checker/> (B) on my SMTP server: * verified for configuration changes * verified that its IP address has a correct PTR record <https://mxtoolbox.com/ReverseLookup.aspx> * verified that its IP address is not blacklisted at Spamhaus <https://www.spamhaus.org/lookup/> * verified normal IP status at Microsoft's Smart Network Data Services (SNDS) <https://postmaster.live.com/snds/index.aspx> * verified that the complaint feed for my server's IP is working properly and that there is no complaint pending in Microsoft's Junk Email Reporting Program <https://postmaster.live.com/snds/JMRP.aspx> (C) test-sent to a non-Microsoft operated domain (e.g. Gmail) and looked at the source of the received message for * DKIM-Signature header (was added by my SMTP server as expected) * Authentication-Results header (return dkim=pass, spf=pass, dmarc=pass) Things that were recommended on <https://mail.live.com/mail/troubleshooting.aspx> and were irrelevant: * Are you sending mail from a new IP? not applicable * Are you running Anti-Virus software? Irrelevant after Outlook returned a 250 confirming receipt * Try connecting to mail.hotmail.com via port 25: Irrelevant after Outlook returned a 250 confirming receipt, nevertheless, just for the fun: nslookup -q=mx hotmail.com telnet hotmail-com.olc.protection.outlook.com 25 * Are you advertising yourself as a non-routable IP? not applicable Other generally interesting information linked or provided by Microsoft that is more relevant to setting up proper SMTP operation than to troubleshooting (and in fairness to Microsoft, it was in their general policies and guidelines <https://mail.live.com/mail/policies.aspx> and not in the troubleshooting section, but still between me and the link to contact the Outlook.com delverability support): General Microsoft Policies (if you are a decent netizens, nothing to worry about) * Microsoft's Service Agreement <http://go.microsoft.com/fwlink/?LinkID=530144> * Microsoft's Anti-Spam Policy <https://support.office.com/en-us/article/Microsoft-Anti-Spam-Policy-e4506f97-694f-49bc-8231-cac4369afcb8> Governmental Regulations: (if you are a decent citizen, nothing to worry about. Check variation for your jurisdiction (Microsoft is US-centric)) * CAN-SPAM Act https://www.ftc.gov/tips-advice/business-center/guidance/can-spam-act-compliance-guide-business * Email Marketers Must Honor "Unsubscribe" Claims <http://www.lawpublish.com/ftc-emai-marketers-unsubscribe-claims.html> Technical Guidelines * Comply with Anti-spam Recommendations for SMTP MTAs (BCP 30) <http://www.ietf.org/rfc/rfc2505.txt> * Comply with SMTP Service Extension for Command Pipelining (STD60) <http://www.ietf.org/rfc/rfc2920.txt> * Sender is expected to comply with IETF standards, including RFC 2821 <http://www.ietf.org/rfc/rfc2821.txt> and RFC 2822 <http://www.ietf.org/rfc/rfc2822.txt> * Do not attempt to retransmit same message to same recipient after receiving an SMTP error response between 500 and 599 (permanent non-delivery response) * Do not open more than 500 simultaneous connections to Outlook.com without making prior arrangements * Do not transmit messages through insecure email relay or proxy server * Unsubscribe mechanism to be clearly documented and easy to find and use * Connections from dynamic IP space may not be accepted * Email servers must have valid reverse DNS record * Sender must not use namespace mining technique against Outlook.com Authentication * SPF <http://www.ietf.org/rfc/rfc4408.txt> * DKIM <http://www.ietf.org/rfc/rfc4871.txt> Reputation Management * Junk Email Reporting Program (JMRP) <https://postmaster.live.com/snds/JMRP.aspx> * Smart Network Data Services (SNDS) <https://postmaster.live.com/snds/index.aspx> All of the above I can checkmark in my setup, so I really can't determine what went wrong. I recorded all this information in this public message, hoping that it will become searchable / easily findable by others in need. I placed my request with the Outlook.com deliverability support and am waiting for an answer. Will report back if there is anything of public interest. Thanks, Yuval Levy, JD, MBA, CFA Ontario-licensed lawyer
