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What can I do so my cat stops peeing outside the litter box?

Ask: I have two cats (male and female) and my male cat keeps peeing outside the litter box. He had the issue for a while and then I got another litter box and he stopped for a while and he started again (a few weeks ago he peed in my closet, a week ago he peed on my boots, and tonight he peed on my dresser).
My vet wants to put him on anti-anxiety meds to get him to stop, medicating was the last resort and unfortunately I'm there.

Does anyone have any advice?

Things to know before you answer... both of my cats are completely in love with each other (so it's not the other cat) and have been for years, I do have two litter boxes that get cleaned every day, he's had anxiety issues ever since I rescued him - if I'm gone for too long or if there's a big change he'll hurt himself (he was abandoned and I rescued him in 5 years ago), and no - I will never get rid of my cat. 


Answer:  
Cosmos Jones: Put a large plastic tablecloth on the floor near the boxes so if he overpees the sides it goes there. You might put an extra box where he peed on your dresser. Sometimes they want to mark that they own that room and will do this kind of thing. 

You can see if redirecting him to a suitable litter option will help. I have done this with some success. It is important to keep clothes and boots up. That is a killer for some households right there. Good luck . I hope he gets better. Cat nip .. and one of those room plug ins might be helpful We ordered these from petsmart.They have pheromones that are supposed to relax your kitty. We tried this with one of our kitties. 


New people will stress cats out as well as new cats. So will changing the seating arrangement if they are certain breeds. 


A dollar store sells cheap party table cloths you can put near the boxes Since I have one arthritic kitty I got a clear under the bed storage container she doesn't have to work to get into and it keeps most of the overspill. I have two 21 year old old kitties and a 12 year old . One started over peeing the box like she is just maybe too senile to notice. I have also experimented with different types of litter containers. I had 8 cats at one time. Crazy cat lady with crazy hat husband.
 


Star-of-darkness: If the cats are not neutered then have them not neutered
Get more litter boxes, at least four and use cat attract litter
have the cat tested for a UTi intend of putting it on meds for an issue that the cat likely does NOT have
 

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