In the past couple weeks, I've noticed a new behavior on transfer detection. Instead of asking me before entering a transfer between accounts during transaction download, Quicken just assumes the latest transfer was to the most recent account. Example: I transfer funds from checking to an investment account at Vanguard. A couple days later, I transfer funds from checking to a different checking account at another institution. Instead of asking me if the matching transactions between the two banks are related, Quicken just makes a transfer between the first checking account and the investment account at Vanguard again. I've attached a screenshot of my preferences so you can see exactly which setting is not working. Also another screenshot of my Quicken version.