The introduction of a speaking and writing test is of greater importance because it is becoming more central to language assessment, especially with reference to communicative language instruction. In order for a writing test to be reliable and valid, the item difficulty should be the same across different test forms. In line with this test equivalence, this study examined the factors that affect writing item difficulty in Level 2 of the NEAT using two qualitative data collection methods, a) focus-group meetings with researchers, professors and teachers who specialized in English education, and b) in-depth interviews with students who took Level 2 of the NEAT. The results indicated that the following factors affected writing item difficulty: a) topic familiarity, b) topic concreteness, c) the extent to which a topic elicits negative feelings from test-takers, d) concreteness of a given writing prompt, e) the extent to which a given writing prompt elicits diverse words, and f) the vocabulary and grammar knowledge required to complete a given writing task. Based upon the study’s results, further research about teaching and testing writing skills is discussed.