Putting aside the narcissistic-masochistic aspiration of authoring a text on all the intricacies of in-depth psychotherapy, I have chosen to address five areas of difficulty in this enterprise. This relatively restricted focus has made it possible to tackle matters in their true complexity and intrigue. The loss of breadth is thus compensated by the gain in depth. The areas I have chosen to explicate pertain to initial assessment, boundaries, money, disruptions, and suicidal crises. Over three decades of clinical experience has taught me that most problems in the course of dynamic psychotherapy involve these areas; their proper understanding and management is key to productive therapeutic work. Each chapter of this compact book tackles one of these areas in detail, outlining not only the conceptual issues at hand but also the technical strategies that emanate from them.