As penetration testers we all want to provide our clients with valuable insights about their environments. This case study of a pen test performed against a health care organization describes how I teamed up with a technical colleague during onsite social engineering in order to further each of our testing objectives. It gave the client stakeholder 'a more complete picture ' than previous tests where social and technical testing aspects were performed well but separately. Our collaboration influenced the pretexts that were developed, the exploits/devices we used, and how we executed them. The presentation will illustrate the handoffs between the social and technical aspects of each approach we took. Attendees will learn about identifying opportunities for collaboration, taking advantage of what your collaborators have to offer, and having fun while adding value for your client.