Apple Mail on macOS not suggesting previously used folders

In my experience it's hit and miss and always has been. As Lawrence says, for similar messages (sender or maybe subject) then it might remember for a period, but there seems to be a timeout and it forgets.

I manage things with rules and smart mailboxes. As an example - I want to be able to manage mail-order shopping. I want receipts to go into my "Receipts" mailbox but I also want to be able to keep a list of undelivered orders so I know what's going on. Here's how I do it.

• I have a Smart Mailbox for New and unread mails and use this as my main view so I can always see new mail.**
• I have nominated one of my flags as "Shopping"
• I have a rule which flags all senders who are in a Contacts group called "Shopping" with the Shopping flag.
• I have a Smart Mailbox which displays all mails which are flagged "Shopping"
• I have a rule which moves mails from Shopping contacts with subject containg receipt, invoice, etc. to my Receipts mailbox.

Here's what happens. eBay is the Shopping group in Contacts. If I get an email from eBay with the words "Order Confirmation" in the subject line heres what happens:

• It shows up in the New Mail smart folder because it's new - and I can see it there.
• It gets flagged with the blue "Shopping" flag and if I go to the Shopping Smart Folder it will appear there.
• It gets moved to the Receipts mailbox.
• Once I've read it the message disappears from the New Mail Smart folder, but is still in the Shopping smart folder.

Once the item has been delivered I simply unflag the mail it and it disappears from the Shopping smart mailbox.

**The "New" smart mailbox also shows all mails with purple flags - which I use as a "ToDo" flag.

It's a rough explanation and needs a bit of tweaking, but works for me. I have similar rules, flags and smart mailboxes for Gig tickets and travel document like tickets, hotel reservations, etc.

It doesn't work as conveniently on iPhone and iPad, but in the inbox you can set the filter to show new and flagged messages only, so all the shopping, gig tickets, travel bookings, etc. are still easy to get at.

If you manually move similar messages to a folder it will remember the folder for future similar messages. It just needs to be retrained.

I need to read and digest what you have written.

Unfortunately I was sidetracked today by a bluetooth issue that prevented me from logging in to my new Mac mini, that took many hours and lots of time on the phone and researching articles in the community.

I'll try (some) of what you recommended and report back.

Thank you.

Update: Spent the past week attempting to retrain the folder action by manually dropping e-mails into the correct folders. Mixed results; mostly not remembering with very few exceptions. I'll continue for another week before giving up.

Huh. So by manually, you mean instead of using the Move Selected Message control on the toolbar to drag and drop the selected message into the proper folder? I'll try and report back. Thank you.