https://www.quicken.com/support/update-and-mondo-patch-20182019-release-quicken-windows-subscription-productto make sure that your software is properly installed.
I had the same issue. I rarely "Quit" my Quicken session, I just close the window. But I found that if I "Quit" Quicken, then when I re-open it, it opens with the Register at the date I had selected/highlighted when I quit. Hope this helps you.