So Mylo is nearly 6 month old, he has been crate trained from day 1 and was always more than happy to go in his crate at bed time which is always around 10pm, some nights he would need out for the toilet but some he would sleep through until morning and we never had an problems, we encourage his to do a pee before bed. About a month ago Mylo caught an infection and had an upset stomach so for 3 nights I slept on the couch with him so when he needed out for the toilet he wouldn't need to wait on me getting up as he was needing out every 30 mins to begin with. After about a week he was over it and back to normal. The problem is every time he goes in his crate at bed time which he is still more than happy to do, he even waits for me to bring his biscuit (which I have always given a small handful of biscuits at bedtime). Once he has finished these biscuits he starts howling, it gets louder and louder and he won't stop, the longest I have left him is an hour hoping he would fall asleep but eventually I have had to get up as I am worried about my elderly neighbour and the noise. To start with I would get up and settle him then head back to bed but he would start howling again. I know I shouldn't have but eventually I ended up on the couch and let him sleep next to me. This has been around a month and you name it we have tried it but he just won't settle. He settles no problem during the day when he is in his crate when no one is home as we have recorded him so I think it is when he knows we are home. Every night myself or my partner end up on the couch with him. I did try giving him long lasting chew bones and that kind of worked as he would fall asleep after chewing but he would only sleep for an hour then the howling would start again. We take him out for walks throughout the day and an extra long walk at night then relaxed playing to settle before bed but it doesn't seem to make a difference. As he is still a puppy and likes to chew everything we don't want to leave him out of the crate on his own at night in case he chews something that could cause him harm, we also can't have him upstairs in our room as it is to hot upstairs for him. He is his usual happy cheeky self during the day but this all started after he wasn't well. Has anyone has similar problems or any advise/ help/ tips would be great as I am willing to try anything.