Hello!
To clarify when certain emails never reach your inbox even after you checked Junk, Rules, and Safe Senders, you need to review your Outlook.com Junk email settings, confirm none of those senders are blocked, and then check Quarantine because Microsoft sometimes holds messages there for security.
If the senders are not blocked and nothing appears in Quarantine, the next step is to ask the senders to confirm their email domain passes SPF, DKIM, and DMARC because Microsoft will stop messages that fail authentication. This keeps your inbox protected.
By the way, do you see any messages inside the Outlook.com Quarantine section when you check your account online?