This report describes a self-study using an action research spiral of problem analysis, intervention design, trial, reflection and analysis. The main purpose of the study was to investigate and evaluate whether Web 2.0 technologies and, in particular, social software could be effectively integrated into a senior secondary English classroom. The methodology used in the study, while mainly qualitative, did include a degree of quantitative data-gathering. The study took place over two terms of the 2007 school year in a semi-rural school south of Auckland. My Year 12 English class of twenty-four students were participants in the study and I was the teacher-researcher. As part of the study the students responded to my 'blog' and created and maintained their own 'blogs'. These 'voices' are important threads in this narrative. Two of my colleagues acted as 'critical friends' in this process. During the study my own beliefs regarding new technology and the descriptor 'digital natives' were challenged. While the data collected and the interpretative analysis of it created further questions that need to be addressed, the findings indicate that there is a place for Web 2.0 technology and social software in English classrooms. The findings also show that in order for these applications to be integrated effectively, a number of issues need to be addressed. My recommendations as teacher-researcher at the 'chalk-face' attempting to keep up with the rapidly changing lives of our students concludes this report.