The expansion of the British military establishment from c. 1730 to 1830 is well known, as is the large numbers Scots and particularly highlanders who formed the British officer class. There is a common assumption—in some respects well founded—that the army had a beneficial impact on the political and economic experience of Scotland. This article offers an alternative interpretation through a focus on the social and cultural implications for highland gentry families of having so many male kin engaged in one particular career. The first two sections examine the scale and increasing attractions of military employment relative to other career destinations, notably farming, the legal profession and trade via urban business apprenticeship. Two generations with different motivations are compared, and the importance of the loss of practical farming and commercial expertise is noted. The next section explores the impact of military employment on relationships within families, particularly between officers and their father or elder brother, but also on relationships with female kin and on the broader processes of family formation through marriage. Of particular significance was the tendency towards teenage recruitment among the highland officer class, which removed boys from the influence of family and gave rise to reckless behaviour, extreme individualism and conspicuous consumption, posing major problems for gentry families and estates. The article concludes that although the military profession was a valuable short-term route for disposing of sons in a gentlemanly manner, the impact on their families and on the highlands could be highly disruptive. Yes, there was success and material benefits for a lucky few, but also tragedy, failure and family discord for many.