There is growing interest in technology that quantifies aspects of our lives. This paper draws on critical practice and speculative design to explore, question and problematise the ultimate consequences of such technology using the quantification of companion animals (pets) as a case study. We apply the concept of "moving upstream" to study such technology and use a qualitative research approach in which both pet owners, and animal behavioural experts, were presented with, and asked to discuss, speculative designs for pet quantification applications, the design of which were extrapolated from contemporary trends. Our findings indicate a strong desire among pet owners for technology that has little scientific justification, whilst our experts caution that the use of technology to augment human-animal communication has the potential to disimprove animal welfare, undermine human-animal bonds, and create human-human conflicts. Our discussion informs wider debates regarding quantification technology.