This paper studies estimation of the conditional mean squared error of prediction, conditional on what is known at the time of prediction. The particular problem considered is the assessment of actuarial reserving methods given data in the form of run-off triangles (trapezoids), where the use of prediction assessment based on out-of-sample performance is not an option. The prediction assessment principle advocated here can be viewed as a generalisation of Akaike’s final prediction error. A direct application of this simple principle in the setting of a data-generating process given in terms of a sequence of general linear models yields an estimator of the conditional mean squared error of prediction that can be computed explicitly for a wide range of models within this model class. Mack’s distribution-free chain ladder model and the corresponding estimator of the prediction error for the ultimate claim amount are shown to be a special case. It is demonstrated that the prediction assessment principle easily applies to quite different data-generating processes and results in estimators that have been studied in the literature.