The main plant species relied on for forage supply to grazing animals in New Zealand and south-eastern Australia is perennial ryegrass (Lolium perenne L.). Perennial ryegrass has evolved with a fungal endophyte (Neotyphodium lolii, Latch, Christensen & Samuals) that occupies intercellular spaces, and is nourished by its host. The endophyte (referred to as standard or wild-type) provides the plant with protection from a range of insect pests by producing alkaloids, some of which are also toxic to grazing animals, causing ryegrass staggers and/or exacerbating heat stress. Over the last 20 years naturally occurring perennial ryegrass endophytes have been found in Europe that produce less of the alkaloids that cause animal health problems but have similar or enhanced effects as the standard endophyte on deterring insect attack on infected plants, when introduced into New Zealand and Australian-bred ryegrasses. This review provides a summary of endophyte research in New Zealand from the perspective of insect pests, plants (particularly perennial ryegrass) and the animals grazed on ryegrass-dominant pastures. The protocols used to evaluate perennial ryegrass/endophyte associations over the past 30 years are also discussed. Future testing of new grass/endophyte associations should include the utilisation of more environments for agronomic and entomological experiments; routinely carrying out small animal toxicology assays, and the running of short-term indoor feeding experiments with sheep and cows. Implementation of these changes provides the minimum requirements for strengthening the evaluation of new endophyte associations so farmers using these technologies, gain optimal benefits from their adoption.