For those with Routines failing, do those Routines also contain Mode changes? If so, I believe that is the problem. I’ve had this issue for the last month, and an open Support ticket almost as long.
The temporary, though cumbersome, workaround is to remove all mode changes/restrictions from Routines and Smartapps, delete the Mode (ensuring first that you’re not in the failing mode), and then putting everything back. I’ve had this restore service for anywhere from one occurrence to a full 3 days. A more permanent “solution” (though still a workaround) is to just forget about Routines, and migrate everything over to the Rule Machine and Trigger Happy smartapps. Unfortunately, neither has the ability at this time to set or change Smart Home Monitor status, so depending on your Routine configuration, you may not be able to move everything over.
Hope this info helps someone, and by all means, if you have a similar issue, report it to ‘support at smartthings.com’ and reference my open ticket (# 54180). The squeaky wheel gets the grease; If enough people complain, maybe they’ll get around to fixing it.