Tammisaari (Swedish: Ekenäs) is a small town on the southern coast of Finland. In my chapter, I attempt to find out what kind of conflicts arose in Tammisaari during the seventeenth century between masters and their male servants, and I also seek to determine how their relationship appeared and developed in official sources in the seventeenth century. I use the terms ‘hired man’ and ‘servant’ as synonyms, although there were differences in later times. The backgrounds of the domestic servants varied a lot in early seventeenth-century Tammisaari. The court cases in seventeenth-century Tammisaari involving male servants consist of two main groups. The first group comprises cases in which male servants argued over their salary or were accused of having broken a promise to enter service. The second group, growing more common from the mid-seventeenth century, were cases of improper sexual relationships. Servants were simultaneously insiders and outsiders in the burgher households. In a legal way, their role as outsiders became clearer during the seventeenth century. Hired male servants were at the same time both obedient servants and opportunists, gamblers in a changing society. Servants tried to balance their own livelihood and advancement in social networks, and this needed both diplomacy and calculation.