Hi Charlie Smith,
Welcome to Microsoft Q&A.
From what you described (it happens in Outlook on the web and New Outlook, and the message can jump back to Junk within minutes), the core of the AI answer is correct: this behavior often comes from server‑side junk filtering, which happens before rules and can also override manual moves.
That said, the AI reply mixes in some work/school “tenant policy” wording that typically doesn’t apply to Outlook for home/personal accounts.
What to try next (quick checks):
- In Outlook on the web, open one of those emails in Junk and choose “It’s not junk” (don’t only move it, this helps train the filter).
- Recheck Settings > Mail > Junk email and confirm your address/domain is listed under Safe senders, and not under Blocked.
- If it still happens, double‑check how the email is being sent (for example: an alias, scanner, app, service, or anything using SMTP/automation). That’s a very common reason messages sent “from me to me” get flagged.
If you reply with how you’re sending those emails (from Outlook itself vs a device/app/service), we can narrow down the most likely cause quickly.
Please let me know if this proves useful to you, or if you would like further assistance.
I'm looking forward to your reply.
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