Certain contacts keep going to junk folder

Using Outlook v16 and SS is working for the most part, but there are still certain contacts of mine that all of their emails end up in my Junk folder. Is there a way to remedy this?

That depends on why the messages are ending up in Junk. You can check the log to see whether it’s because of SpamSieve. If not, it may be because of a server junk filter (which you could perhaps turn off) or a rule on another Mac or device.

Thanks for sending the log file. It’s not clear to me which messages you are saying are incorrectly in the Junk folder because it does not look like you trained any as good. It’s important to correct all the mistakes, both for filtering accuracy and for troubleshooting purposes.