cat urinating outside litter box

Hello,

Here is the run down and what i think is happening. Any help on this would. Be appreciated.

I have had this 3.5 year old a total of 5 days. I also have a 7 month old kitten and they are from the same household but i have had the kitten for a month. The older cat uses the litter box sometime. Matter of fact i have been worried that he was having a problem because i haven't been cleaning urine from the litter box that much. My roommate just came in and told me he sat up from his hidin place and he thought that he was coming out to say hello but he was just urinating. The smaller cat, who use to follow the older cat around before i got him, is now being a little jerk and walking up and hissing at him.

The older cat is still very scared and doesn't come out if we are around and awake. We find him sometimes in different places but he seems to go back to my roommates room to hide under his night stand. The smaller cat sleeps with me, otherwise i would have put him in my room to begin with.

What can we do to make the older cat relax and stop urinating outside the litter box?

let me get this straight, the older cat don't come out of his hiding places when you  guys are up, so he just pee where he at instead of using the litterbox? 

This is normal behavior for a cat you have had 5 days as far as the hiding is concerned. Give the older cat a private place of his own with little traffic in the house assuming he runs under a bed in that room Id put his litterbox close to being under the bed on one side and food and water on the other side. He will eventually come out and the litterbox can be moved farther away from the bed or whatever he is hiding under.

Urinating outside the box is cause for concern. Have you had him checked out by the vet to rule out medical issues?

How many litterboxes do you have? Minimum two, ideally three.

Is the kitten ambushing or otherwise causing anxiety to the older cat when he is using the litterbox?

How often are you cleaning the box(es)? You said you "haven't been cleaning that much". Minimum once every day, ideally two to three times a day for two cats, depending on output.

How many times has he gone outside the box (you said he uses it "sometimes")? Is this the first time or has this been going on (in which case stress may be a factor)?

The older cat has used the litter box in the past. This was the first time that he did it in front of us. He did it once a little when i first brought him home but i figured he was just stressed. Also let me make a note of how i got him health wise. He had fleas (many), tape worms and a urinary trac infection. He escaped because of the movers letting him out, was caught about 4 days later ( very cold outside) stayed in one home, taken to a vet the next day, then taken to another home for 2 days before i got him. He has been through a lot. He is in his new home with 2 of us and the 7 month old he use to live with.

We have 2 litter boxes, one for each cat seperated. They are also. Fed separately because the older cat has to have wet food because Of his Urinary Tract infection. I'll get another litter box if you think it would help. The other cat, as far as i know, hasn't attacked the older cat while he has been in the litter box. The younger cat gets close to the older cat and hisses at him. They use to be friends from my understanding. As a matter of fact the younger one use to follow the older one around. Oh, the older cat has only gone outside the box once, but i think it is more because it smells like urine in other locations of the house. I clean the litter boxes usually twice a day. Once in the morning and once when i get home from work. I am also feed them on the same schedule. I have had to clean the older cats out as much because he hasn't been using it as much.

after you get the litterbox problems solved and everything else try reintroducing them http://www.thecatsite.com/a/introducing-cats-to-cats

Re-introducing them is a good idea. Despite them having lived together, sometimes a change in environment (like moving to a new home) can completely change the dynamics between two cats. Best friends can become mean to each other.

It seems the poor baby has gone through a lot, so keeping him in a separate room (with his food, water, toys and litterbox) during introductions will help immensely with stress (see above link about introductions). Considering that he's just arrived in his new home, everything and everyone probably smell strange to him. A room where he can hide in solitude until he's ready to feel safe may be just what he needs. Let him hide, don't try to force him out to socialize. He needs to hide until he feels ready.

A third litterbox wouldn't hurt. Some cats like to #1 in one box, and then #2 in another box. Some cats won't even use the box if another cat has already used it. With regular scooping (twice a day as you are doing is great), having more litterboxes ensures that each cat always have a choice.  

the older cat has only gone outside the box once, but i think it is more because it smells like urine in other locations of the house  

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Possibly. Even if we can't smell the urine, a cat's nose is very sensitive. Any soiled spots should be cleaned thoroughly with an enzyme cleaner (like Nature's Miracle -- see our Reviews section if you could use brand suggestions) so that the cat won't be tempted to go in a previous spot. 

Here's another article, perhaps something in here you could use:

http://www.thecatsite.com/a/litterbox-problems-in-cats-the-ultimate-guide

Thank you for your advice. I'll keep everyone posted. Best to all!

My cat Raven had something quite similar. The vet recommend a product called Feliway (at least that's what I think it's called) and he said that it helps cats to relax and of it's in the spot where they keep urinating, they should stop shortly.