Life experiences and living conditions can influence the problem-solving strategies and the communicative abilities of dogs with humans. The goals of this study were to determine any behavioural differences between Labrador Retrievers living in a kennel and those living in a house as pets and to assess whether kennel dogs show preferences in social behaviours for their caretaker relative to a stranger when they are faced with an unsolvable task. Nine Labrador Retrievers living in a kennel from birth and ten Labrador Retrievers living in a family as pets were tested. The experimental procedure consisted of three "solvable" tasks in which the dogs could easily retrieve food from a container followed by an "unsolvable" task in which the container was hermetically locked. Dogs of both groups spent the same amount of time interacting with the experimental apparatus. Kennel dogs gazed towards people for less time and with higher latency than pet dogs; however, there were no significant preferences in gazing towards the stranger versus the caretaker in both groups. These findings demonstrated that kennel dogs are less prone to use human-directed gazing behaviour when they are faced with an unsolvable problem, taking the humans into account to solve a task less than do the pet dogs.