After nearly a decade of war in Afghanistan, military and government officials have described the propaganda efforts of the Taliban insurgency as increasingly sophisticated and effective. These statements fail to distinguish between insurgent propaganda efforts at the local level and those carried out online and targeted at Western populations. This research investigates the effectiveness of the Taliban's use of English-language media to reach Western populations and shape their own image in a way that furthers their strategic objectives. An analytical approach that combines quantitative analysis performed on a set of Taliban messages from 2007 to 2010 and a deeper, qualitative assessment of a subset of those messages provides insight into the trends and themes within Taliban messaging. This approach shows an unsophisticated Taliban English-language propaganda effort that, despite showing recent signs of potential improvement, has failed to shape its image in support of its strategic objectives, focusing its efforts instead on violent and reactionary messages and following a narrative driven by the Western and international media.