This little monster is called Dexter.

He’s a lovely cat, really. A bit whiny, slightly skittish, but otherwise very nice. He likes skritches and laps and is generally very polite when there isn’t a door he wants to be on the other side of.

Unfortunately he also has a variety of exciting bladder problems. He’s currently on a five pill a day regime in an attempt to sort this out.

Dexter does not like pills.

We are lucky in that one of the things Dexter does not do is attack people. He might injure you in an attempt to get away when sufficiently panicked (ask me about bath time for kitties), but he never actually attempts to harm you no matter how much he disapproves of your actions.

Nevertheless, we’re engaged in an arms race. It used to be the case that I could just cradle him in my arms, stick a pill in his mouth, and he would swallow.

That is, uh, not the case any more.

Here is our current cat pilling protocol, presented in case it will be useful to others.

You will need:

• Two people. Don’t even think about trying this with one. We are considering whether adding a third person to the protocol would be useful.
• All of the pills extremely conveniently to hand.
• A dropper pipette with water in it. A syringe would also work but you need to be good at not squirting it excessively.

There are two people in this protocol. For sake of avoiding ambiguity, I will refer to them as David and Dave. David is sitting, Dave is standing. The role of David is cat control, the role of Dave is pill application.

1. David cradles the cat in his arms lovingly. He pretends this is to lure the cat into a false sense of security, but actually the cat knows exactly what is about to happen.
2. David sits down with the cat flat on its back and head pointing away from him, wisely exposing his belly to the sharp back legs (you may wish to take protective measures if you have a less polite cat than Dexter).
3. David grabs the cat by the scruff of the neck. If the cat does not look in mortal terror for his life at this point from how much his face is being pulled back, David has not grabbed enough scruff.
4. David traps the front paws, which the cat has learned to move while scruffed, under an arm and levers the cat’s jaws open.
5. Dave swiftly moves in, drops a pill into the back of the cat’s throat, and follows with a squirt of water.
6. David holds on very tightly. The first time we squirted water into Dexter’s mouth he somehow teleported across the room.
7. David prises open the cat’s mouth to check that the pill has indeed been swallowed.

Something about the squirt of water seems to cause Dexter to instantly swallow. This appears to be a general phenomenon according to the internet.

In order to understand these drastic measures, here is a list of things that don’t work any more or never worked:

• Dexter is terrible at eating. He doesn’t really do it. He certainly doesn’t do it if you try to feed him from your hand. As a result none of the standard “wrap the pill in food” measures have ever been effective on him.
• Cat burrito is not a useful control procedure for Dexter. We used to try to use this to control him, but it just freaks him out more because he knows exactly what’s about to happen. We end up having to reset the burrito between each pill, which causes him to freak out more. It’s easier to just hold his legs in place with body weight and, if necessary, hands.
• Releasing his scruff, holding his mouth shut and stroking his throat results in him very helpfully makes swallowing motions. You then later discover he’s stored the pill in his cheek.
• Anything that allows him to move his jaw. He chews up the pill and starts foaming pill residue at the mouth. If we didn’t know the cause of it, the sight of our cat foaming red at the mouth would have been quite unsettling.

I expect the current protocol is only going to work for so long before Dexter figures out how to not swallow when you squirt water into his mouth. Fortunately I expect to have moved out by then.

Edit to add: I had to pill the cat solo tonight. The burrito technique worked… well at least it worked better than trying to handle the cat without the towel. The experience was significantly less pleasant for both human and feline participants, but I didn’t have enough hands to do it any other way.