Poor Shadow.
Ripley can feel her pain. Although he did have a slight bladder infection the vet and I still think a lot of his spraying issues are stress from the new kittens and being bossed around so much by Scout. Scout seems to just hate him, there is no other way to describe it, and poor Ripley won't really stand up for himself often. Things between them have gotten better but I thinks it's just because Scout has become too lazy to always annoy Ripley.
I use the Feliway Plug-ins and spray (not so regularly anymore) and we've started letting Ripley go out into the garage to use the bathroom and have some alone time. Also my vet has prescribed Valium to help him chill while recovering from the bladder infection. It's done wonders for him, he no longer cares if Scout bothers him. Unfortunately we will run out of that next week. I may call and ask for more but I don't know how long is good for him to stay on it.
Best of luck. I hope you come up with a good daytime solution. Look into the Feliway and if the vet does or even doesn't find an infection ask about Valium to help her chill out a bit.






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