The purpose of this corpus-based study is a bottom-up investigation of strategic devices used by heritage language speakers (HLSs) during narration and conversation. It offers a critical review of compensation/communication strategy definitions and classifications, and presents the results of an investigation into strategies employed by an under-researched target group, that of HLSs. The study is not based on any a priori classification scheme; rather it is data-driven. Conversation analysis used to analyze the data revealed, among other, that the 70 Greek HLSs, a heterogeneous group with diverse linguistic, cultural, and affective characteristics from the U.S. (Chicago) and Russia (Moscow and St. Petersburg), employed 14 strategic resources. All three communities used the same strategies, except for loanblends, which were used only by HLSs from Chicago. The latter also exhibited a more frequent use of strategies overall. We conclude that, in spite of their linguistic challenges, the HLSs were capable of achieving their interactional goals. HLSs generally have opportunities to use HL in the community/family, which enriches their strategic repertoires and facilitates language production. However, not all HL environments are language conductive and, as a result, HL learners' curricula should provide explicit strategy instruction in order to increase their speaking skill.