On-line item generation is becoming increasingly feasible for many cognitive tests. Item generation seemingly conflicts with the well established principle of measuring persons from items with known psychometric properties. This paper examines psychometric principles and models required for measurement from on-line item generation. Three psychometric issues are elaborated for item generation. First, design principles to generate items are considered. A cognitive design system approach is elaborated and then illustrated with an application to a test of abstract reasoning. Second, psychometric models for calibrating generating principles, rather than specific items, are required. Existing item response theory (IRT) models are reviewed and a new IRT model that includes the impact on item discrimination, as well as difficulty, is developed. Third, the impact of item parameter uncertainty on person estimates is considered. Results from both fixed content and adaptive testing are presented.