Wish I could help but I had this and other potty issues with Ava for nearly a year and I tried many different things. The only dog/puppy I was not able to housebreak quickly. I never figured it out and we explored possible medical issues also.
No pee last night. Went to bed at 1030, set alarm for 1230. No pee in crate -Took him out, he peed. Set the alarm again for 0530, no pee in crate. Took him out and he peed and poop. Went back to bed and up at 0700. Out to pee. 0845...out to pee and poop. Since I was off yesterday (injured finger), I fed him at 730PM vs. 830 PM. I can't imagine the hour making a huge different but I guess I'll never know since I took him out at the 2 hour mark. I'd like to stretch the 0530 to 0700 but I was afraid to push. Wanted success last night for both of us. :-)
Hooray for a successful night! Sometimes it's a relief just to know success is possible!
My dogs aren't fond of me interfering with them trying to pee either but first thing in the morning, they usually have to go bad enough that they're like, "whatever" Hope there's no UTI and he's just still being a baby.
When we got Maverick he was the easiest puppy ever. Bear, not so much. He fought against going to bed at night. He'd just scream in his crate like he had to go out. He'd carry on for a good half hour. He didn't pee on his night time crate either. We did the same as you, only we had an ex-pen. He didn't pee on his day time pen but he always peed on the floor of his ex-pen. And pooped. Eventually what worked was just taking the extra space away during the day and forcing him to hold it. At night we started crating him in our room. It was us he wanted, not Maverick. With us and Maverick and Bear all together he just went right into his crate and quietly went to sleep.
As far as going out at night, set your alarm a few minutes later each night to eventually eliminate the outings. He'll get there!
At least you know now, and it wasn't his fault. Poor little man. Make sure you get a follow up urinalysis in a few weeks after his course of antibiotics, to make sure the UTI is gone.
He will feel better very fast!
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