The editor of MacAsgaill's posthumous 1961 poetry collection, Alick Morrison, is also the poet's first biographer and has left behind a detailed account of his childhood in the Outer Hebrides during the early 20th century.
According to Ronald Black, the culture clash between the Gaelic oral literature taught at the Ceilidh houses and the Anglicisation enforced through corporal punishment in the schools after the 1872 Education Act is crucial to understanding Iain Eairsidh MacAsgaill and all other Gaels of his generation.
As Alick Morrison wrote, "Gaelic culture reigned supreme all over the island except one spot; it stopped dead at the threshold of Berneray Public School.
[2] Three of his fellow pipers were killed and eighteen were wounded, but, even though the ribbons were shot off of MacAsgaill's pipes, he survived the Battle of Loos unscathed.
After four years, in 1923, he left the police force and returned to Berneray,[4] where he worked as an agricultural laborer for Reverend Tormod Moireasdan[2] and began for the first time to versify in earnest.
Most of his Gaelic poems and songs were composed during this period, in which MacAsgaill suffered greatly from homesickness and bitterly regretted his decision to leave behind the happy life he had known in both Berneray and Glasgow.
[4] At Dr. MacAsgaill's request, acclaimed bagpiper John D. Burgess visited the grave during a tour of Australia and played a lament for the deceased poet and piper.
[7] After first reading her great-uncle's Australian poetry of homesickness during a Gaelic class held in Glasgow,[8] Alina NicAsgaill Simpson took the initiative to repatriate MacAsgaill's remains to Berneray, Harris.