Several people have posted here about how scheduled updates are not running correctly. Symptoms include the double arrow sticking in the system tray and the quicken scheduler not asking for the vault password on a reboot. Instead, the vault password prompt shows up the first time the scheduled download was to happen.
Today I stumbled across a clue. I had disabled UAC to track down a different problem. When I rebooted with UAC off, the Quicken password vault window showed up right after the reboot.
Too soon to see if the double arrows stick around, but interesting if UAC is interfering with the Quicken scheduler.