Hi Mandy, as Pearly has said – getting him more used to his ‘new’ situation (with less dependence on you) now should help. To (hopefully) help allay your fears, my 2 and a half year old cocker has recently adapted to being an outside kennelled dog during the day when I am at work. This after having been inside up till now. He is outside with my young dog, and while there was some initial unsettled barking, he is now quiet (according to my neighbours and dog walker ), and is more than happy to go in there in the morning. I have a dog walker visit at lunch time to let them out and check on them – you may want to do the same. It gives me peace of mind too. I’d put Ted outside (perhaps on the vreandah) with some toys and a filled kong/hoof – something to keep him occupied - and slowly extend the time you do this. Also maybe start feeding him out there so he associates the experience with positive things. Suppose it’d be quite similar to teaching a puppy that when you go out, he goes into a crate with a kong. They are very adaptable – and while it may be a bit upsetting to hear him cry (if he does at first), I’m sure he will settle fine with a bit of time and patience. Hope it goes well, and you have a good restful holiday.