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After spending days backwards & forwards with Support for the Outlook desktop app (Windows 10), they have admitted that the issue is with outlook.com...!
Because you can't turn OFF Automatic Filtering - either Standard or Strict - message Rules won't run automatically on emails that outlook.com has automatically sent to Junk!
For goodness sake, Microsoft, please allow users to turn Automatic Filtering OFF completely so that your own Rules actually work...! At the moment I have to run Rules manually every day to Permanently Delete the deluge of daily Spam emails I receive from the same domains again & again, buried deep in the message header...!
Sending, receiving, and organizing email in Outlook.com
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The only way to contact Microsoft directly is https://support.microsoft.com/contactus and click the Microsoft 365 icon. It should (eventually) get you to a chat.
Hi. I'm Brian and I'll try to help.
Rules work automatically only on messages delivered to the Inbox. That's always the way it has been for both Outlook online and desktop Outlook, either classic or new. You can run rules manually for any folder, but they'll run automatically only for Inbox messages as they arrive. If you have messages that arrive in the Junk Email folder that you want rules to process, then mark the sender or the sender's domain as a safe sender or add the sender to your Contacts. That will cause them to be delivered to the Inbox, where your rules will see them.
If they truly are junk, obviously you don't want them delivered to the Inbox. The Junk Email folder is the correct place for them in that case. There is no way to prevent the delivery of spam and never has been, since files don't work for non-Inbox messages and "blocked" means "delivered to the Junk Email folder." If you can't live with how Microsoft handles that, then make a suggestion at https://feedbackportal.microsoft.com/feedback (or upvote any similar suggestions) or look for a mail provider that allows you to do what you wish.
All the more reason to let users turn Automatic Filtering OFF, so that messages will land in the Inbox and the 'Permanently Delete' Rules I created will work!
Most of the 'Senders' use a string of random letters such as 'qmzpnwoxebic@rvuskalhffqg' in the From field, hence digging into the Message Header to find some common ground...
Thanks for the Feedback link - for all the good it will do!
Paid services are better at that type of operation. A business using a Microsoft 365 for business tenant would probably have more control over that as well, but I don't know that with certainty.
I pay a Family subscription for Microsoft 365 - used to have a standalone subscription for Outlook - which now includes Outlook and has increased in price 'hand over fist' the last few years, apparently to pay for CoPilot (the only 'improvement' I've noticed!) which I don't want and have never used...!