Domestic dogs (Canis familiaris) have been shown to actively initiate triadic communicative interactions by looking at a human partner or by alternating their gaze between the human and an object when being faced with an out-of-reach reward or an unsolvable problem. It has hardly been investigated, however, whether dogs flexibly adjust their human-directed behavior to the actions of their partners, which indicate their willingness and abilities to help them when they are faced with a problem. Here, in two experiments, we confronted dogs-after initially allowing them to learn how to manipulate an apparatus-with two problem situations: with an empty apparatus and a blocked apparatus. In Experiment 1, we showed that dogs looked back at their owners more when the owners had previously encouraged them, independently from the problem they faced. In Experiment 2, we provided dogs with two experimenters and allowed them to learn through an initial phase that each of the experimenters could solve one of the two problems: the Filler re-baited the empty apparatus and the Helper unblocked the blocked apparatus. We found that dogs could learn to recognize the ability of the Filler and spent time close to her when the apparatus was empty. Independently from the problem, however, they always approached the Helper first. The results of the present study indicate that dogs may have a limited understanding of physical problems and how they can be solved by a human partner. Nevertheless, dogs are able to adjust their behavior to situation-specific characteristics of their human partner's behavior.