I think you should first take him back to the vet. The fact he has a history of urinary problems means he could easily have one of several urinary tract problems, including stones or obstruction.
Diet alone won't prevent UTI and other problems from recurring.

Yes, first rule out UTI or blockage, which is fatal.

Also, the vocalizing while he is peeing may be an indication of win.

Good luck and let us know what the vet says.

indication of pain.

A friend's cat always pees on clothes when her UTI is active, another vote for a vet check.

Also, from someone who's suffered w/a cat that peed on furniture, I learned to keep rooms closed off from her. Shut your bedroom door when you're not in it. Good luck, it's rough to deal with.

Thanks everybody! I wasn't even sure anyone would respond lol I'll talk to my vet after the weekend. I can't really close him off from the bedroom without locking everyone away in their room. I dont think thats fair to my other cats. I sprayed down my bed with air freshener and that has seemed to keep him away so far lol Guess he doesn't like that smell. Keeping my fingers crossed!

Sorry you're going thru this. They learn to associate the box with pain, and sometimes they will continue even after the pain is gone. If so they have to be re-trained to un-do that learning. Let us know if that is the case and how he checks out at the vet.

if your cat is squatting to urinate, it is most likely due to bladder pain and not a 'bad habit' or 'bad' behavior. Cats that urinate due to anxiety or some other stressor tend to spray against vertical surfaces, such as walls or furniture (even female cats will do this). But squatting to pee, particularly if he persists despite your trying to actively scare him from doing it, are almost always signs of suffering from bladder discomfort. So you need to be taking him in ASAP to be sure he is indeed able to empty his bladder completely. As someone already said, blocked cats are emergencies- can be fatal if not attended to right away.

Not sure what 'special diet' you are giving your cat now, but you can never go wrong with a fish-free canned food, and would recommend switch to that ASAP as well. If you are feeding a special dry, try to switch again to the same diet, but in canned form. I have been treating blocked cats and cats with painful bladders for over 20 years and nothing works better prevention-wise than canned food (and no fish if the urine shows any signs of struvite crystals). However UTIs (true bladder infections) are extremely rare in young cats (only seen maybe 4 in 20 years in otherwise healthy cats under the age of 10) compared to maybe 500 cases of FIC (feline inflammatory cystitis- a non infectious cause of bladder pain and bloody urine). So hopefully your vet will not just put your cat on antibiotics and hope that takes care of the problem.