Why doesn't Quicken Mac Deluxe (Subscription) automatically enter categories?

@GH23 This has been an unusually frustrating problem for Quicken Mac users. The product manager acknowledged it, and promised some forthcoming relief, awhile back. but there has been nothing released in an unusually long time.

For what it's worth, it has nothing to do with the change to the subscription model. As best I know, the developers broke something about auto-categorization in an update last fall. It seems like it's not completely broken for all users, but a lot of what used to work doesn't.

You can experiment with the technique which used to work to see if it still works for you: manually create a transaction for a Payee you recently purchased from, for the same amount and date, categorized as you want it. When you download the transaction, drag the manual one over the downloaded one, and Quicken will merge them into one -- and will also learn this mapping to apply on subsequent downloads to the same Payee. I can tell you this used to work, but I don't know if it will work for you currently. If it works, while it's a pain to set up for a lot of Payees, once you do it once, it will save you a bit of time.

The alternative is to wait for the developers to deliver a more comprehensive solution. The product manager has acknowledged the need for, and confirmed they are working on solutions for, allowing users to define rules for Payee renaming and for learned (memorized) categorization. these changes apparently involved some significant changes to Quicken's architecture, so it's taken a long time to implement. We still don't know which features will be delivered when; we only know help is coming. 

It's a bit odd that there hasn't been any comment from Quicken about this pretty significant feature being broken for a long time, but posts from Marcus are few and far between.