It only takes as long as you noticing them consistently going in the litter box. At least it does for me, anyway.
When I first got the kittens, Belle had her own little issues. She had a bit of a rough start and being rejected by her mum, didn't help any.
By the time I got them, the only living thing Belle trusted was Sadie her step sister.
While Sadie had no issues going in the litter box, Belle would just seem to go where she was. I had just about covered my whole lounge floor in tin foil (rolls eyes). I followed her as much as I could but catching her in the moment was really hard to do.
Finally, I just decided that after every meal I will sit her in the box till she goes. That seemed to miraculously work! We would celebrate, make a big deal of her success and reward her with a nice juicy treat!
Life was good.
A couple months later, I was beginning to allow them to go outside. Everyone had to learn to use the great outdoors. Eventually they did, B U T Belle seemed to forget where the litter pan was when it was time for them to be inside!! ARRRGGHHHHH!!
Now she was older, and I had to catch her in the act and relocate her to the box. After a few days I managed. She only had 3 places she would go, so when she would "wonder off" I followed her. I caught her and just calmly picked her up, put her in the litter box, let her do her thing and again, reward her for her efforts.
I did the follow thing for a week, maybe two. But everytime I scooped the litter box, Belle was always watching me (she's my helper lol) so if there was anything in there, I didn't care who did it, I would tell her what a good girl she was, pointing at the box and the poo and generally let her know I was well pleased. I usually snuck in a little treat as well.
It seemed to work for us. I mean to this very day I will still tell her what a good kitty she is whenever I am cleaning out the box. Odds are she is the one who has used it anyway, everyone else seems to have bladders the size of an Olympic pool.
But I don't go around looking for "stuff" anymore, I trust her to go where she needs to go.
On them noticing if you trust them? I don't think it's that kind of an issue for them. I think they are busily trying to figure out what it is you are wanting from them. I believe they struggle, like we do at times, trying to figure out what is being communicated.
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