29 karma · joined January 15, 2020
Thank you all for the suggestions.
On my "quarantine" I can't find anything (it's empty) therefore I can't also check what's going on. But "URL detonation reputation" is consistent with the behavior we're observing.
If the recipient is using a personal microsoft / outlook / hotmail account the email gets delivered with a spam score of 9.
If the recipient is a MS 365 account, blackhole it is.
We even set up our own MS 365 to prove this.
We do use Azure for small stuff, but too small for any special support channel.
Message Trace is an interesting one.
If we send an email without the 25friday.com keywords everything works fine, the message is shown on Message trace as delivered and the recipient gets the email with SCL 1 (all good here).
As soon as the very same email is appended with a www.25friday.com, Message Trace still shows the outbound email, also as delivered, but the recipient (if a Microsoft account) never gets the email. We used one of these emails (EML) to create a submission on the defender portal of a false positive, but they always simply disappear with 0 feedback (and the problem still occurring).
We also had a signature with the www.25friday.com link on it and took it out after realising it was causing emails to go to this black hole, so that at least we can still send emails, but we keep having to be careful to never sending any content (or attachment) that somehow mentions the 25friday.com domain.
I guess I'll try to submit a report anyway using Googles' outbound IPs.
We do have subdomains for internal tools of course, but those should not even be publicly accessible (behind an auth proxy).
This book was written to make developers think and consider their choices, not a script for good code.