Have you ever tried a pet piller/pill gun? A vet friend of mine suggested that to me as one of my cats gets daily meds but grew wise to pill pockets.
I have this one and it works great: Cat Pill Gun
DJ knows he will get a treat afterwards so he doesn’t care. When he hears the pill bottle he hops up on my desk or a table. I gently grasp the back of his head/neck (basically to steady his head, not restrain him), slide the tip of the piller in the corner of his mouth to open it (sort of like deworming a horse) and shoot it in. He then demands his treat.
It is so much easier than trying to just use your hands. I think it also helps with him being at the same level as me and I’m sitting down so he doesn’t feel overwhelmed. I did some counter-conditioning with the piller first so that he associated it with treats, then I gave him some treats with it, and then switched over to the pill.
He gets some other meds in his food and I use Churu for that.