This course reviews federal income US tax considerations affecting owners of and lenders to troubled businesses. We start with a discussion of rules concerning debt restructurings, and their implications to lenders and borrowers. We review considerations concerning the protection of valuable tax attributes, such as net operating loss carryovers. We then cover approaches for harvesting tax benefits for losses on entities and investments. We then describe certain hazards that can arise in capitalizing on a troubled entity. Finally, we discuss potential personal liability to management and other responsible persons for “trust fund” taxes. The course is designed for accountants, managers, financial professionals, investors, CFOs, and other professionals who operate, invest in, or otherwise are affected by, businesses and investments in financial distress.