Housebreaking Dogs

Any tips for housebreaking dogs? Am I doing something wrong?

My dog is almost 5 months now, I’ve been trying to housebreak him since I got him when he was 2 months old. I followed dog books saying to use positive reinforcement, you know praising him when he goes outside, only punishing him if I catch him in the act while inside, and if I don’t catch him just clean it up myself. Now he’s 5 months old, shouldn’t he be housetrained already? I read they were able to hold their bladders longer now, but he doesn’t seem to be able to.I take him out 3-5 times a day because I exercise my other dog a lot, but my puppy doesn’t ever last the night; I always wake up to having to clean pee. I have him on the same schedule as my other dog, who went through the same training and did just fine! So what am I doing wrong?
Edit: Yea I used to put him in the crate, but I thought he’d be fine without it now, I guess I’ll go back to using it. :/

In addition to the crate, I would also cut him off of water at night…maybe 6 or 7pm? We’ve been working with our 1 year old and have had him for a month…he has never been housebroken! So far so good, but even he still has the occasional accident. At first they were happening so often that now any time we let him out of his crate we immediately take him outside to empty out before he can play or do anything else! I guess it’s just a matter of patience and time at this point!

How to House Train a Puppy : Consistency & Positive Reinforcement in Housebreaking your Puppy