I recently setup scheduled updates to run one step updates at night. I have been doing it manually and that works fine, but the scheduled updates never run. I have it setup to run every day at 5:00 AM. I have Windows 10 (ver 22H2 build 19045.4046) and Quicken Classic Deluxe R54.16 build 27.1.54.16.
In the schedule dialog box for the password, I selected "At Windows Startup". I've rebooted my computer since setting this up, but that didn't help.