This article is derived from the qualitative portion of a larger study conducted on mathematics websites that provide expert volunteer help. Data consist of tutoring logs of five expert tutors from two help sites, plus interviews with these tutors. The researcher has employed theories about expertise in the educational domain to elicit details of individual coping strategies with challenges posed by the online environment, including students' non-responsiveness and issues of academic honesty. One of the participants, a recent online tutor who was also a teacher, experienced conflict of professional interests between these two roles. Tutors, who were also students, felt a conflict of liability--towards the tutees on one hand and towards the website administration on the other. Except for one tutor who demonstrated a highly developed expert performance, other tutors exhibited characteristics of both novices and experts, thus placing themselves within temporary and context-dependent locations on the novice-expert continuum. Recommendations are offered herein for future research and for the organization of online tutoring environment. It is suggested that best practices must include both pedagogical and tutor training/support considerations. (Contains 3 tables and 1 note.)