In 1998, Massachusetts instituted a $20,000 Signing Bonus to address concerns about the supply of quality teachers. This article reports on a longitudinal, qualitative study of the experiences of 13 of the original 59 recipients of the Signing Bonus, and analyzes their responses to various incentives embedded within the Massachusetts Signing Bonus Program (MSBP). Interviews revealed that the bonus money had very little influence in recipients' decisions to enter teaching. Far more important was the alternate certification program created to implement the policy. Findings suggest that the MSBP: (a) relied too much on inducements and not enough on capacity-building; (b) focused too narrowly on recruitment and not enough on retention, and (c) centered too much on individuals and not enough on schools.