Just curious about this but, how would S/o react to the skeleboys if they just dozed off or just passed out due to either overworking themselves or just an extreme lack of sleep. Btw I love your head cannons. I hope this gets answered soon.
Sans: When he sees you passed out on your desk, he would nudge you a bit. If you're out cold, he'll use his magic to pick you up and take you to his bed so you both can cuddle together~
But if you wake from his nudge he would tease ya about going to sleep. If you refuse, he would playfully nudge ya to join him in his world famous naps. You debate but seeing how he smiles at you and holds your hand in his so tenderly, you can't help but agree.
Papyrus: He would glare down at your passed out form at first. then he would take your sleeping form to your room. Tucking you in as softly as he can as to not to wake you. He then organizes the mess on your desk. Just so when you wake up everything isn't in complete dismay. He debates on joining you but decides on making an entire speech for when you wake up as to how to take better care for yourself and how much he cares about you.
Red: If he catches you sleeping, he would poke you awake. Or at least bug the hell out of you till you wake up. Once you do, he'll ask you to join him to bed. If you're too tired he will just teleport you two and he'll trap you in his koala bear hugs. There is no escape for you once you're in his hold.
Boss: He would yank you away from your desk, no matter what you say. He would set you on the bed, ignoring your dismay as he organizes your mess. If you're still up he will go and fetch you a glass of water so you're hydrated before finally falling asleep. ofc he'll cuddle with you cause he can't resist holding you in his arms.
Nox: He would lecture you as he takes you away from your desk and sets you on the bed. Even lecturing you as he kisses your head and cheek saying how much he worries about you. Then forcefully wrapping you into a burrito so you have no way of escaping. But alas you give in and sleep - much to Nox's success. But when he saw your sleeping form he couldn't help but stay by your side and watch your sleeping form. Seeing you this peaceful makes his heart flutter.
Rus: He's just as bad as you so if anything, he would be the most understanding when you say how DEEPLY tired you are. He would ask for cuddles - straight off the bat. He gives you his biggest puppy eyes and you give in ofc. You two ignore the mess and he just takes you two to bed where you two fall asleep in each other's arms.
Blue: His loud booming voice would have woken you up. But once he notices your lack of energy and how tired your are, his demeanor softens and his mother hen instincts kick in. He makes you some remedy tea that helps sooth your body and then takes you to bed. (yes he carries you, you have no say in the matter) He makes sure you're nice and comfy and hangs out with you until you finished the tea. Once you are he would tuck you in and stay by your side. He debates on staying longer so he can cuddle with you but.... oh what the heck he can steal a few hours of nap time with his s/o.
Stretch: He would try to coax you to move away from your work. If you refuse he will let you be. Waiting till you finally succumb to your slumber then he will scoop you up in his arms. He will lay you on the bed and cuddle with you. If you wake he will lull you back to sleep with his kisses and humming lullabies.
Ash: When he notices how tired you are he would be very instant in getting you to bed. His worrying attitude makes you melt seeing as he's literally petting your face and hand as if you might fall on him. You're his delicate flower after all. Eventually if you follow along with him, he would tuck you in. He would make sure you have water and if you ate anything. Once he sees you're falling asleep he stays by your side. Seeing your sleeping form also got him a bit tired... maybe he can have a small nap and get back to gardening later...
Poplar: When he sees how tired you are he would be very persistent in bringing you to bed. Even so much as TRYING to yank you away. But what breaks you is his tone of worry. He sounds so sad when he tells you how much he worries about your health and that he wants you to be happy and healthy. He loves you too dearly to see you get sick. You agree to go to sleep, Poplar happy to see you finally leave your domain of your desk. He would tuck you in. Mother henning you the entire time and making sure you're taken care of. He even says he'll set an alarm so that way you don't oversleep. You thank him before passing out. Ofc when he sees your sleeping form he can't help but stare longingly. He stays by your side a bit. He's not exactly tired, but he doesn't want to leave your side... So he decides on getting a book and some tea and join you in bed. That way he can hold you close while also keeping himself entertained.