This paper discusses illegitimacy and single motherhood in the postwar period in the Netherlands from the perspective of what was considered to be in the interests of the child: being adopted by a married couple or being raised by the birthmother. It focuses particularly on the impact of psychiatry and the legalization of adoption in 1956 on the emancipation of the single mother and her child. The paper argues that the release of single motherhood and illegitimacy from the moral-religious stigmata of a “sinful fallen woman” and a “damned” or “degenerated” child has, in the Dutch case, not proceeded as a linear process. The process of emancipation toward proud and independent lone motherhood stagnated in the 1950s and 1960s because, when adoption was legalized, illegitimacy became an issue over which scientists, especially psychiatrists, gained the power of expert control. Guided by dynamic psychology and what they conceived of as the best interests of the child they declared single mothers to be victims of “sociopathology” and, consequently, unfit for motherhood. Adoption became the preferred option. This medicalised approach continued to dominate until the reawakening of feminism in the late 1960s made self-sufficient lone motherhood once more a respectable choice.