The windings insulation of electrical machines will remain a topic that is updated frequently. The criteria severity requested by the electrical machine applications increases continuously. Manufacturers and designers are always confronted with new requirements or new criteria with enhanced performances. The most problematic requirements that will be investigated here are the extremely long lifespan coupled to critical operating conditions (overload, supply grid instabilities, and critical operating environments). Increasing lifespan does not have a considerable benefit because the purchasing price of usual machines has to be compared to the purchasing price and maintenance price of long lifespan machines. A machine having a 40-year lifespan will cost more than twice the usual price of a 20-year lifetime machine. Systems which need a long lifetime are systems which are crucial for a country, and those for which outage costs are exorbitant. Nuclear power stations are such systems. It is certain that the used technologies have evolved since the first nuclear power plant, but they cannot evolve as quickly as in other sectors of activities. No-one wants to use an immature technology in such power plants. Even if the electrical machines have exceeded 100 years of age, their improvements are linked to a patient and continuous work. Nowadays, the windings insulation systems have a well-established structure, especially high voltage windings. Unfortunately, a high life span is not only linked to this result. Several manufacturers’ improvements induced by many years of experiment have led to the writing of standards that help the customers and the manufacturers to regularly enhance the insulation specifications or qualifications. Hence, in this publication, the authors will give a step by step exhaustive review of one insulation layout and will take time to give a detailed report on the standards that are linked to insulation systems. No standard can provide insurance about lifespan, nor do any insulation tests incorporate all of the operating conditions: thermal, mechanical, moisture and chemical. Even if one manufacturer uses the standards compliance to demonstrate the quality of its realization; in the end, the successful use in operation remains an objective test. Thereafter, both customer and manufacturers will use the standards while knowing that such documents cannot fully satisfy their wishes. In one 20-year historical review, the authors will highlight the duration in insulation improvements and small breakthroughs in standards writing. High lifespan machines are not the main interest of standards. A large part of this publication is dedicated to the improvements of the insulation wall to achieve the lifespan. Even if the choice of raw materials is fundamental, the understanding of ageing phenomena also leads to improvements.