Analogical comparisons between the American experience in Vietnam and in Afghanistan are rife in the media, but it remains unclear how effective analogical reasoning is in understanding the contemporary challenges in Afghanistan. The literature illustrates that while analogies can be helpful in understanding problems initially, adherence to stark analogical reasoning often blocks a fuller understanding of a complex problem that generally differs when one goes beyond superficial analysis. Thus analogical arguments that Afghanistan is nothing like Vietnam or that Afghanistan is just like Vietnam contribute little to our understanding of the challenges faced today by U.S. and NATO forces. This article looks at the contemporary application of the Vietnam analogy to Afghanistan and its utility in understanding contemporary security challenges.