Unrepresented parties in litigation struggle with legal doctrine and puzzle over procedure. Judges provide some assistance in court, but they must exercise restraint so as not to raise questions of bias or favouritism. How do judges manage these interactions in the decision-making process? This article examines sample cases from one common law jurisdiction, Singapore, to identify the litigant in person (LIP) typologies in court-LIP interactions. There are likely a number of typologies that guide a court’s assessment and response to an LIP, but this article focuses on the typologies most relevant to judicial decision-making on legal issues, legal knowledge and credibility. Because legal knowledge and credibility typologies help courts evaluate LIPs, they assist courts to make decisions regarding unrepresented parties and allow cases to proceed to judgment. However, the typologies are not able to completely address the deficiencies LIPs bring to the dispute resolution process.