Cannot get ex-feral to use the litter box!

Whattado

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A cat showed up at our house last summer and was pretty wild. He wouldn't let anyone come near him and would run from us. Long story short, my son and I kept working with him bit by bit and finally got him where he is now a big baby. I have no idea how old he is but he is a big boy. He is still afraid of things and terrified of anyone that is not us but he is a huge love bug with us. My problem is that he will not use the litter box. I have another cat (a female) who uses the box right in front of him so I know that he knows what it is. This has been going on since November when I was finally able to get him to start coming in the house. He has been in the house permanently since December (he has been fixed and has all shots--checked out as great by the vet so no health issues). I have a litter box in the house and one on the porch. The boxes are extremely clean as I am way too diligent about cleaning them!

I take him outside to use the bathroom. I never thought that such a thing ever occurred with a cat but I take him out like a dog. He lets you know when he needs out by standing at the door, looking at the handle and meowing. He goes with me, digs his hole, does his business and goes back to the house. He does go outside in our fenced yard some during the day (my mom watches him as she is home while I am working). I assume that he goes to the bathroom outside at some point during the day as well. He sleeps with my son at night. Amazingly, (knock on wood), there have not been any accidents either. All of this is well and good unless it is pouring rain outside or snowing or I want to go on vacation for a few days. It's impossible because he won't use the litter box and only wants to go outside to do his business. I don't know what else to do. No one could ever come stay with him because he is terrified of everyone besides my immediate family. I couldn't take him to a cat hotel to board because I feel it would be cruel to him and he wouldn't use the box there either. If he would just use the box, it would alleviate a lot of problems because I could just have someone come to my house and care for him so I could go away and it would keep me out of the pouring rain as well!

Does anyone have any advice at all on how to encourage a cat that has used the bathroom outside his entire life, to start using the litter box? I have had many cats in the past and never had this issue. Of course, I have never took one from basically a feral state to being a pet either.
 
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Whattado

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I completely forgot to tell you the names of my cats!

The kitty in my profile pic is Snowball.
The kitty that I am referring to in my post is named Other Kitty.
 

susanm9006

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Maybe you could try putting a litterbox outside with sand and dirt in it just to see if you can get him used to using a box. If you can get him to that point you might be able to move that box indoors And hopefully he would continue to use it.
 

FeebysOwner

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Or, to the semi-reverse of the above, place a low sided (to start of with) litter box containing the soil/sand/etc. that 'OK' is used to going in, and even placing some of his "outside pee/poop' inside that box. You can start with one that is close to outside, and as said above, gradually move it - pretty much inch-by-inch inside.
 
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