Notwithstanding over 20 years of propaganda promoting board school teaching as an ideal career for upper-class women, it appears that in the 1890s it was still unusual for "girls of good family" to go in for it. Therefore, it was an eccentric plunge in 1898 when Eglantyne Jebb, an Oxford student from a prosperous land-owning family, enrolled in Stockwell Teachers' College. An understanding of recruitment and retention patterns and the hurdles faced by women teachers across the social-class spectrum requires more studies of individual careers. Eglantyne Jebb's short teaching career documents in detail the process of becoming a board school teacher and the deep-rooted class boundaries that Jebb felt branded her as an "outsider." Viewed from the vantage point of history, her problems were probably compounded by unsympathetic peers, a dearth of role models and enthusiastic but ill-informed mentors. All of which may offer some insight into why so few women of her background found their way into and stayed in the profession. (Contains 128 footnotes.)