Thank you for the additional information. This is a difficult problem, but one that can usually be resolved. I was dealing with the same thing with a female I have that would use the litter box to urinate in but always deficated on the floor - usually right next to the box. As frustrating as it is to deal with, it can be fixed. First, you truly need to rule out any medical problem such as a urinary tract infection or blocked anal glands that may be contributing to the discomfort he's feeling. This may be a throw back to when he was declawed as cats sometimes associate the pain in their feet after surgery with the litter box so they stop going there.

Once your vet has given him the 'all clear' as far as health is concerned, you need to do a couple of things. First, purchase a second litter box. Some cats feel the need to urinate in one box and defecate in another. When you get the second box, use a litter in it called "Cat Attract". It's fairly new, but it is what turned my girl around. It's a simple scoopable litter that is treated with something they find very attractive and we have not had a single incident of going outside the box since we started with it 2 months ago. It even has a money back guarantee, and truly is amazing.

You can purchase Feliway Plugins for the house also in addition to the new box and litter. They put out phermones that are very soothing to cats and this too may help with his misplaced litter habits. If there is anything in the home that changed around the time this started, it may be those changes that triggered the problem. Cats react strangely to stress, and going outside the box is the only way they have to express their displeasure. I would definitely NOT put him outside at ALL while you are trying to recondition his behavior. If there are any cats within smelling distance, their scent alone can be enough to trigger bad behavior and habits, so the more distance you can put between him and potential problems, the better.

Since he is neutered, the problem is definitely not hormonal. Make sure you clean any area he has soiled with an enzymatic cleaner such as Zero Odor (www.zeroodor.com) or he will continue going back to those places. If the behavior does not improve with the above suggestions, discuss with your vet the possibility of putting him on medication for a short time that may help with this. Many people find a medication called Buspar to help greatly with litter box issues, and your vet may feel that it's appropriate to try it if everything else fails. I'm pretty confident that he will start using the box routinely as long as it's kept clean and my suggestions are followed. Please let me know how he does!