do you have 10 speed/strength on that loop, or is it speed level? Levelling the skill (the number on the right) only makes you gain the skill value faster on a given loop. You still need to get to 10 speed or strength that day to pass the check, so even on speed lv.100 you need to queue some action that will level speed before you can keep up with Chronobunn
(also yes this is not clear from the game tips as is, it's implied in the game description in the "to help you get started" list but I missed it too initially)