This article presents research from a qualitative study exploring five secondary English teachers' professionally oriented participation online. Drawing upon Cole's (1996) "surround" and "weaving" views of context, the specific line of research featured here was guided by the following question: What are the features of the online contexts that selected secondary English teachers weave in exploration of teaching, learning, and literacy? The author collected archived online artifacts (e.g., blog posts, microblog posts, and posts within social network sites) and employed an ethnographic content analysis. Findings revealed five notable contextual features that emerged across cases: multimodal affordances and a/synchronous flexibility, as seen from a surround view, and classroom teaching experiences, connections among teachers online, and a touch of levity, as seen from a weaving view. While providing directions for future research, these findings stand to support more nuanced understandings of the teacher-generated online environments to which many educators are turning in an effort to supplement their professional growth.