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With the diabetes diagnosis for my cat, we got a whole new routine. I used to feed him his wet food at 6-7 am (basically whenever I got too annoyed by him trying to wake me) and then he would free feed dry food the rest of the day.

Now, he is on a much more controlled diet. He gets wet food and a bit of dry at 9 am and 9pm, when he also gets his insulin dose. They have to be at the same time because he needs to eat directly before the insulin, and I can't change the times I do the insulin as it has to be a 12 hour spacing and with my work schedule, 9pm is the earliest I can do it in the evening as that's literally a few minutes after I get home.

The thing is, this makes him...frustrating in the mornings. Now he wakes me up, and I have nothing I can give him to placate him so I can go back to sleep. I don't want to have to lock him out of my room, that's not the point here. I just want to figure out how I can make it clear that I am not getting up. I tried telling him no and putting him on the floor, I have tried spraying him with water, I have literally tried everything. I am hoping he will adjust eventually, but in the meantime I am kinda frustrated with the sleep I am losing.

How can I help both me and my cat adjust to our new reality?

While I haven't handled a cat with a diabetes diagnosis, I've handled routine changes many times with multiple cats (including sleeping schedule changes and switches from free-feeding to scheduled feedings), and ultimately what you need to do is out-stubborn your cat.

You say your cat is waking you up in the morning. He's become accustomed to being fed at that time, and you need to now break that cycle. He knows he can get you out of bed, and that his chances of getting fed are improved when you're out of bed; what you need to do is stay in bed and ignore him. It's going to be difficult, especially at the start, but to break the habit you have to stop responding entirely. No telling him no, no moving him, no spray bottles. Pretend you're still asleep. I've had solid, repeat successes in fairly short periods of time getting cats to stop waking me up for food using this technique. It does take longer with an adult cat with an established routine, but once you're able to establish this new routine of "I will get up when I want to, not when you want me to," future routine changes will be much more straightforward.

If or when he starts begging for food at other times, you similarly have to be more stubborn about it than he is. This should be easier to resist, but similarly, ignore him if he gets insistent about the lack of food in his bowl. With time, he'll start to learn the regular feeding times, and will start reminding you of them when they're coming up, but he'll stop begging the rest of the time.

Unfortunately and as you probably suspect, the only thing that is going to help with the adjustment is time...

He was on the old schedule for a long time, getting used to the new schedule is going to take a while.

If you want to replace the 6-7AM feeding with something else, I recommend grooming. A daily brushing, petting and massage, should keep his interest for a while. After a while he we learn that waking you up at 6AM leads to grooming not food. Food happens at 9AM. He will adjust.