I adopted Miles in July of 2016 from a shelter when he was 2 years old. I don't believe the questionnaire the prior owners filled out was completely truthful. He was not very affectionate but their answers said he liked other cats. I waited 4 months and then adopted Jasmine in November of 2016 when she was 7 months old. Miles ended up having suspected inflammatory bowel disease, insulin dependent diabetes (for the last year and a half) and play aggression towards Jasmine. Miles needs 3 medicines to keep him from severe vomiting and not eating. He also needs an insulin shot once a day. I have spent thousands of dollars on him at the vets and I do love him but Jasmine is a much better companion to me as I live alone. The problem I'm having is when Miles gets in one of him amped up moods he chases Jamine, jumps on top of her and tries to bite her. He's not growling and hissing but she is. Just recently I've noticed that she has peed on the carpet where the ambush took place because she's so upset. This has been going on for a long time but the urinating is new. I've tried playing with the cats, I've tried Feliway, I've tried toys that move but Miles still does his ambush from a few times a week or more. When he's not ambushing her they get along fine. I'm going to try giving Miles Solliquin soft chews on the advice of a vet tech. Does anyone have any other recommendations? If I can't get his behavior under control I'll have to try and re-home him which is unlikely due to his medical issues and expenses or make the heart wrenching decision to have him put to sleep. Both cat are fixed.