Emails from One Contact Going to Junk Folder

David:

The "Junk Mail" settings you have been telling us about, those are all set within Apple Mail. Right?

And those are the same as you've been using for longer than the last "week or two". Right?

Then. All this could be explained by AOL starting to use a new "Junk Mail" filtering system, in that time frame.

I recommend you log into your AOL Email account, through a browser, and see what "Junk Mail" settings your email account has set, at that end.

(They may even have a new "policy" or other announcement concerning "Junk Mail".

I'm sure they believe they are trying to help you, their customer.)

Joey C 2:

Those settings look reasonable.

However, a few notes:

1. Check to make sure the headers in the messages from that person are not declaring the message as Junk! By your settings, that may override the sender being in your Contacts or your Previous Recipients.
2. Make sure the email address exactly matches what you have in your contacts!

If there's no problem with the aforementioned potential issues, then we've got more "digging" to do: like what mail service you are using and what "Junk Mail" processing they may perform even before it gets to your device.

The reason AOL's setting overrule your Contacts is because your Contacts are specific to Apple Devices (their on iCloud). They are not AOL's listing of your Contacts.

It's one of the problems with multi-layered email processing! AOL has their processing before the email even gets to Apple Mail!

The simplest thing to do, Joey C 2—provided AOL permits it—is to completely turn off AOL's "Junk Mail" processing.

Otherwise, you'll need to go to AOL, now and then, to "fix" such issues.