In Windows 10, my Quicken 2016 developed an annoying bug. The first time I would try to load it, it would fail with this message:
Quicken encountered a problem while starting and needs to close
The second time I would try to load it, it would work properly.
Any fresh reboot of Windows 10 would start the cycle all over again.
Here's what I did to fix it: I ran Ccleaner to clean up my resources and registry.
I don't know what exactly the problem was, nor do I know what fixed it. I only know that Ccleaner fixed it.
Probably some other similar app would work just as well.