An analysis of postings on the LM_NET discussion list was conducted to better understand school library media specialist (SLMS) perceptions of the potential effect of structural challenges on their role in teaching Web evaluation skills. Structural challenges are institutional in the form of government regulation and school culture, and are defined in terms of a three facets: (1) high stakes testing; (2) "everyone in charge, no one in charge" (in which professional roles and school norms vary or are poorly defined); and (3) limited access to digital media. Results reveal relatively little discussion of the effect of high-stakes testing despite the high profile of this issue in the education literature and the mainstream media. The "everyone in charge, no one in charge" category garnered the most emotionally charged responses and was further subdivided into discussions of professional standards and of defining and defending professional roles. The limited access category addressed externally imposed limitations (generally in the form of filtering software) as well as the occurrence of self-limiting behaviors and choices. A prevailing theme throughout the discussions was the "workaround," in which SLMSs attempt to get by or even thrive within a set of circumstances that are beyond their control. (Contains 1 table.)