Mortgages, student loans, credit cards: debt is a ubiquitous component of daily life in Canada. But our attitudes toward debt, and the people who incur it, are complex. Trustees at Work explores the role of bankruptcy trustees in determining who qualifies as a deserving debtor under Canadian personal bankruptcy law. When debt becomes unmanageable, the bankruptcy and insolvency system provides relief – though not to everyone. The architects of the system have restricted access to this benefit by developing methods to distinguish deserving from undeserving debtors. The idea of a deserving debtor is reflected in the law governing the bankruptcy and insolvency system, which seeks to provide debt relief to the deserving while withholding it from the undeserving. In practice, however, trustees tasked with administering bankruptcies focus largely on how cooperative debtors are during the legal process in making their determinations of deservedness. Using insights from the sociology of emotion, Anna Jane Samis Lund reveals how carrying out emotional labour shapes an insolvency professional’s assessments of a debtor’s deservingness. Trustees at Work also includes interviews and statistical data that update and expand the research on insolvency professionals. Ultimately, it shows how insolvency trustees’ conceptions of a deserving debtor are shaped by the financial, legal, and emotional contexts in which they work.