Working with clients who have complex health concerns and presentations encourages us to adapt and shape protocols over time to support our client’s unique needs and goals. With complex cases, some effects of the herbs can be slow and incremental while other effects can be fast and obvious. How do we know which herbs are doing what? What does a client centred and harm reduction approach look like when working with people who depend on drugs that are potentially harmful and often stigmatized? How do we address our client’s health concerns alongside prescribed pharmaceutical medications or substance dependence? This class goes through the case of a client who I worked with for over a year, primarily on insomnia, leg pain, hypertension and opiate addiction. I hope for it to stimulate discussion about the above questions, and more.