A computer‐simulated software training system (CSSTS) delivers a specific form of computer‐based training in which participants are allowed to select various training features within a simulated software environment. Given the growing use of these systems as end‐user training (EUT) aids, there is a need for greater understanding of how participants use these systems, as well as whether participant‐controlled learning environments are truly effective. The present research examines how a particular learner characteristic, software self‐efficacy, drives appropriation in a high learner control, CSSTS environment. Contrary to notions in the literature, results from spreadsheet and database software training courses reveal that pre‐training specific software self‐efficacy constitutes a significant, negative predictor of faithful appropriations of the CSSTS. This research also establishes a positive relationship between faithful appropriation and increases in software self‐efficacy (SSE). In essence, faithful appropriations lead to greater increases in SSE, which influences software skills performance. In addition, the research validates prior EUT research by extending prior findings to a database training environment. A psychometrically sound measure is put forth to capture database self‐efficacy.