We have been fostering cats for a few years now. Though we are far from experts, some of the fosters have “challenges”.
Does Pepper use all the litter boxes? It could be a scent thing.
Does Puddles…puddle in the boxes without issue? Have you been able to watch Puddles pee and see if he goes into the box or if he pees from outside the box too?
From your description of him being a little anxious, I’m guessing on a couple of things:
Sounds like you’ve used various boxes, I’m assuming you’ve tried high and low sided boxes and larger boxes? It’s possible he feels anxious pooping, maybe because he feels trapped. A larger flatter box might help.
Also sounds like you’ve tried different litter too…have you tried different litter and type of box permutations? Perhaps the sound of the litter against the box bothers him? You could experiment with different cardboard boxes instead of buying more plastic boxes to see if you can determine a combo.
Also on the litter front, he maybe doesn’t like the feel of certain litter types on his feet. If you have a large box has you tried just putting litter in the back half of it or the middle third to see if he will at least go into the box? This idea falls apart of he pees fine inside the box. The Feliway spray is also a good idea to try.
While you’re trying to figure it out, can you put the box on top of a large rubber mat or a large piece of extra floor vinyl? The ideal would be putting the main box into a bathtub but you are in a condo so that’s likely out. Our resident cat was a standing pee-er and the combo of a large high sided rubbermade box with a door cut into it and placing the box into our basement bathtub was effective.
If you like, I can reach out to my foster peers to see if anyone has a different idea.
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