Over the past decade, the health index has become an increasingly popular asset management tool in utilities. The health index as a condition indicator can improve the decision making process. However, it also has challenges which need to be considered during development and implementation. This paper addresses the advantages and disadvantages of the health index as a condition indicator in a critical discussion. Moreover, a case study is presented where a health index is calculated for three transmission power transformers. The case study illustrates that age and the load factor included in the health index calculation lead to an immoderately high health index for the transformers T2 and T3. Thus, the paper ageing of the transformer windings are used instead which results in a plausible condition representation of all three transformers. The case study also demonstrates that the observation of condition trends over time is lost if the health index is transformed into a linguistic expression.