I never found anyone of consequence who would agree with me or admit that it happens, but I will continue to swear that this is a feature of Hotmail/Outlook. The first time I identified it I think was in 2013. A customer reported the same behavior from their HostGator VPS (when I worked there). I had a test Hotmail account so I logged into their VPS and sent myself an email. Microsoft accepted it, but it was nowhere to be found. Not the spam folder, inbox, nothing. I moved another domain to their VPS temporarily and sent mail from that domain, and it was received. To me that drew the conclusion that this was related to the reputation of the sending domain in Microsoft's systems.

We're not alone:

https://answers.microsoft.com/en-us/outlook_com/forum/all/mail-not-received-outlookcom-response-to-sending/fd4211a6-c8e6-41fb-a94e-8254706f2ec1

https://answers.microsoft.com/en-us/outlook_com/forum/all/messages-reported-as-250-queued-for-delivery-but/f451cda5-ba7d-45ff-b643-501efe2413dc

https://answers.microsoft.com/en-us/outlook_com/forum/all/sendgrid-says-emails-delivered-but-customers-with/62de80ab-c006-4507-86d1-708d255c996d

https://answers.microsoft.com/en-us/outlook_com/forum/all/email-accepted-by-hotmail-but-not-delivered/83621726-60f8-46ce-9416-daf2385acca3

I for one would love to see this topic validated, but all I find across the internet seems to be gaslighting like "Is your SPF correct?"

On 2023-12-01 22:36, Randolf Richardson, Postmaster via mailop wrote:
Some of my users have been reporting that eMail messages are getting
lost intermittently when they're sent to users at any internet domain
name that relies on OUTLOOK.COM for its MX.

        Our mail server logs confirm that all outbound messages were
accepted to those MX's (except for mistyped addresses or when a
user's quota is exhausted, in which case the usual SMTP rejections
occur).  No bounces were received.

        Users have also reported the same intermittent problems when sending
from other providers (including GMail, YahooMail, etc.).  No bounces
were received (as far as I know).

        We signed up for Microsoft's SNDS over a year ago, and added the
IPv4 addresses of our mail servers (unfortunately IPv6 is still not
supported, so more than 50% of our outbound SMTP connections won't be
included in whatever statistics are supposed to be provided by SNDS).

        After logging in, the "View Data" section indicates the following:

                No data for specified IPs on this date

        In the past we were able to download a few CSV reports using the
links in the "Automated Data Access" section, but now they're only
presenting empty files (0 bytes).

        Does anyone know if this just a temporary problem with SNDS that
occurs from time-to-time, or is there something more that we need to
do to get meaningful results from SNDS?  (The ChatGPT AI support bots
have not been helpful.)

        Thanks.
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