Can you please share the IP address the email was sent from?
On the one hand, it's possible for a feature we call, "Time Travel" to work in 
a similar fashion, after detecting a campaign, but that would move the email to 
Junk and not delete it entirely.
Since this is a recent incident, it's possible the automated system hasn't 
gotten back to you with a ticket (SRX#) yet, but that should happen relatively 
quickly.

Under some circumstances, especially for traffic being sent to a, "mail sink" 
account that never sends mail, etc, there can be strange behavior.

But we really need the sending IP address to get a better handle on what's 
going on.

Aloha,
Michael.
--
Michael J Wise
Microsoft Corporation| Spam Analysis
"Your Spam Specimen Has Been Processed."
Got the Junk Mail Reporting 
Tool<http://www.microsoft.com/en-us/download/details.aspx?id=18275> ?

From: mailop <mailop-boun...@mailop.org> On Behalf Of Ricardo Signes
Sent: Friday, March 29, 2019 7:02 AM
To: mailop@mailop.org
Subject: [mailop] mail to Outlook accepted, then vanishing

Hiya,

Lately, we're seeing a lot of mail from us (FastMail) being accepted by 
Outlook[.com], but then never reaching its destination inbox.  It's not in a 
junk folder or somewhere else.  It seems like Outlook is accepting the mail and 
then dropping it on the floor somewhere.  Obviously, this isn't great for out 
users.

Here's an example SMTP interaction between us and Outlook:

2019-03-29T09:44:11-04:00 gateway2 postfix-out/smtp[3294666]: A421222096: 
to=<operatester...@outlook.com<mailto:operatester...@outlook.com>>, 
relay=outlook-com.olc.protection.outlook.com[104.47.1.33]:25, delay=2.3, 
delays=0.05/0/0.69/1.5, dsn=2.6.0, status=sent (250 2.6.0 
<c6883afe-2d47-40b2-be0d-73b897c7f...@beta.fastmail.com<mailto:c6883afe-2d47-40b2-be0d-73b897c7f...@beta.fastmail.com>>
 [InternalId=18708877624108, 
Hostname=VE1EUR01HT199.eop-EUR01.prod.protection.outlook.com] 10961 bytes in 
0.465, 23.013 KB/sec Queued mail for delivery -> 250 2.1.5)

We've filed a ticket, but I don't think we've had any response, and it's a 
scary problem, since we can't detect anything to tell users.  Anybody know what 
can cause this behavior?

--
Ricardo Signes (rjbs)
Postmaster, FastMail

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