Some messages consistently going to spam

Catalina 10.15.7 (19H2) - gmail account, using Apple mail. I have checked Apple Mail settings and I am complying with each and every line. Filtering is disabled in Gmail. I have whitelisted the addresses at issue and check blacklist for anything that might stop them.

If there are specific addresses that you want me to look at, you can send them to me via private message. But, generally speaking, looking at the diagnostic report that you sent, I see:

  • Some messages that you trained as good that SpamSieve had not processed at all. This could be because they were caught by a server spam filter. Please observe in the future when you “Train as Good” whether the message is in the Spam mailbox under “On My Mac” that SpamSieve uses or in another mailbox.

  • Some messages that you trained as good that SpamSieve had thought were spam. You have SpamSieve’s whitelist enabled, so presumably these addresses were not on the whitelist. I also see conflicting information, e.g. you received multiple messages from the same sender, which SpamSieve thought were spam, but you only trained one of them as good. It’s really important to correct all the mistakes because otherwise SpamSieve will learn incorrect information, and the filtering accuracy will decline.

Thanks for sending the report. It’s clear that these good messages were not caught as spam by SpamSieve:

  • They are not listed as Predicted: Spam in SpamSieve’s log. The log shows that, when it sees messages from those addresses, SpamSieve has classified them as good due to the whitelist and your Contacts.
  • They do not have the colored background in Mail’s message list, only the brown text color indicating that another filter marked them as junk.
  • They are in the Junk mailbox, not the Spam mailbox that you’ve configured SpamSieve to use.

So, most likely, the messages were caught by a server junk filter.