Quicken continues to improve auto-renaming and auto-categorizing downloaded transactions from banks. One issue that persists: I use the transfer feature A LOT to link balance transfers between accounts (e.g. Checking to Credit Cards, Checking to Pay Pal or Venmo). Quicken is auto-categorizing my these 'transfer' transactions in my Checking account properly; however, a linked transactions is not appearing in the other account (see Checking and Venmo screenshots below).
In order to remedy this, I have to recategorize the 'transfer' transaction in my checking account to something else (i.e. Uncategorized), save it, then recategorize it again as a transfer (i.e. [Venmo]). Then a linked transactions is generated or matched in the other account.