When's the best time to feed a dog when locking him away a night?

When does he usually pee and poop after eating? And why won't you be able to take him out during the night if he needs to go?

I urge you to feed two main meals a day - splitting the daily amount in two. Mine are fed at around 7 am, and the second before 5 pm. Digestion in the dog takes, usually, 4 hours. As one of mine started upchucking bile during the night, I now give him a small amount of tinned Chappie (UK) last thing - that's stopped all that. They both, correspondingly, have two, or maybe 3 bowel movements during the day - and yes, they are crated in with me, at night. Always have, always will as I don't want unexpected mistakes when I'm sleeping (with them elselwhere).

I can't comment on him living outside most of the time - I just don't see the point having a dog and not having him in with me, or outside, with me.

When you normally feed him at night what time does he poop? I feed my digs at 5 am and 5 pm and they empty about 7 andagain 7 pm. Every dogs different.

Have you tried feeding him a half portion of food for breakfast and against dinner?

Also unless there is a medical condition he shouldn’t need crating at night, even stubborn dogs are trained by 2 years.

You also mentioned bringing him in st night, do you usually keep him free outside 24/7? Your lucky some wildlife had not seen him and made him dinner. We have hawks and eagles, not to mention coyote and fox, wolf that love taystee snacks. They got the neighbors poodle last month when it was running outside with its owners,

Why are you crating him at 5 years old? And why isn't he housebroken at that old? WTF????

It takes 12 hours to digest a kibble meal but only maybe 4 hours for canned (maybe less since canned is 75-80% water). I would NOT feed the canned meal at night or certainly NOT close to bed time, if you do not intend to allow him out to go potty if needed overnight, despite a very WATERY night meal.

Despite it being his supposed preference (for only 1 meal or 1 kibble meal) if you added warm water to some of the canned & made into a gravy and then added it to an equal ration of kibble (twice a day) I bet he could get used to eating every 12 hours - which is HIGHLY recommended for small & toy dogs - who are PRONE to low blood sugar. Two equal meals in carbs & protein; fed about 12 hours apart would also help prevent wild blood sugar swings and help you predict when to expect a BOWEL movement.