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We had a dog who completely froze if he had anything more than a collar and lead on him. Have you tried attaching a very light lead on him in the house and then garden and just letting it trail so he can get used to it being attached. Lots of rewards with high value treats, we find coked chicken to be a winner, but some dogs seem to be sensitive. We’ve had a couple of rescue dogs that were anxious and we found a thunder vest or even just an equa fleece t shirt helped calm and give a bit more confidence, again getting used to wearing it in the house first. We have a Digby too 🥰- he usually loves his walks but if it’s dark he does his business and then turns for home- not that I’m complaining😀.
 
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