It's a hard situation and I've only had to go through it once with my dog.
It seems like a cliche but for us it was true...you'll know when it's time. And more importantly your pet will let you know when it's time. When we made the decision the life had gone from his eyes and he clearly wasn't enjoying life anymore.
If you come to this decision do yourself a favour and accompany your dog and be with him when it happens if you can. It will make you feel better and provide him with the comfort he needs for this final hurdle.
It isn't easy.
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