Be sure you’re supporting his back bunny-feet when you try. They feel safer knowing they can spring away, and are therefore less likely to struggle. Because cats. Also if they get away, they’ll land better so they don’t get scared for next time. If nothing else they’ll be training you to be a fun springboard, so be sure to carry them to something good like their favorite level of the cat tree.

I started cradling him when he was just old enough to be adopted. Every time we crossed paths, I would say “Scoop!”, scoop him up with a hand under his chest, roll him over backwards with my other hand on his butt, and lay him down on my arm like that. Then I’d scratch his tummy and give him kisses, then let him go after a little bit.

Two of my cats had upper respiratory infections as kittens, and I would spend a few minutes with them cradled in my arm while I scraped gunk out of their eyes and noses so they could see and breathe better, and giving them their medication.

By the time they were over their colds, they would just lay there quietly, patiently. They seem to like being held that way now.

My eldest cat often has a little discharge in the corner of his eyes. I’m having some limited success doing the same thing, just gently grooming his face with one hand, while scruffing him on his side or back with the other. He prefers wrestling to cuddling, though. He tolerates me touching his face only if I have my hand on the back of his neck. As soon as I let go, it’s wrestling time again.