Well I have a question, did you keep them locked up for 10-14 days inside the 10X10? This usually gets them associated with "home". If not try it now. Otherwise, yes they will get the idea of roosting, (late bloomers) put up a perch about two feet off the ground and keep them in longer in the mornings. This also helps with getting them used to "home" and the perch is enticing when evenings come.

What do the poor things do when it rains?

I think the problem is that the birds do not see the pen as "home". The situation should improve when they have a proper chicken house... unless they get too used to roosting just anywhere.

Even when they get the chicken house, they will need to learn that it is home. Closing them in at night could be a chore for a bit.

I suggest you try an interim solution. Will the chicken house be going inside the dog kennel? If so, I think if you were to get an appliance carton and close it all but a "pop-hole" (chicken door) and a bunch of ventilation holes that they may use it, once they are in the pen. They should feel safer inside it than in the open.

And rather than rounding them up AFTER they start camping out for the night, why not take some special treats down to them close to their bedtine, stand inside the pen and call "Heeere chick-chick-chick!" Once they get used to that routine, getting them settled should be a lot easier.

As a general rule, it is far better to get the housing built BEFORE you get the critters. You'd save yourself a lot of headaches.

I thought with my ducks I would have to go round them up every single night at first, then one night I went out to do the round up and there they were inside thier house quacking quietly for me to come and close the door for them! I never had to round them up again.
Now however, they are in a pen shared with goats, and the coons etc, stay away from the goats, so I don't have to round them into the house, they go inside the barn and sleep on the goats, yes ON the goats!

Just start calling them with some feed in your hand of a pan and get them used to going in for a bedtime snack....they will eventually start getting there before you do...

Keep their food and water inside the pen and leave the door to it open during the day so they can come and go as they please, but must go in there to eat or drink. That way they learn to associate the pen with 'home'. Just before dusk either feed them or sprinkle some fresh food in the pen. When they go in to eat, close the door behind them. :)

Is it possible that the roosts are too high, too large, too small, etc.?

Velvet ~:>

My chickens have a shed with laying boxes and a perch with a ramp leading up to it. Their food and water are in the shed and they go into the shed to eat, drink and lay. However, come dusk they cuddle up together in the dirt outside the shed. For weeks I put them on their perches and they stayed there over night but the next night were back outside. After a while I could just put them in the shed and they would get onto their roost and stay. However, after many months they still do not go to the shed to roost, instead stay outside cuddled together. Winter is approaching and I am concerned.

Any advice? I have read a lot of articles but I have not read about chickens that will roost wall night when put there but won't come in by themselves