The study examines a corpus of 306 request emails written by 32 English-speaking (ES) teachers and 121 L2 learners from distinctive L1 backgrounds (i.e., Chinese, French, Spanish) and with different levels of L2 proficiency. Pragmatic competence is analyzed through the coding of direct and indirect request strategies used in formal and informal email writing. Findings reveal the influences of communicative situation, L1 background, and L2 proficiency on pragmatic competence in email writing. First, L2 learners show a significantly lower degree of situational variability compared with ES teachers. Second, L1 backgrounds have a significant impact on L2 writing performance. Third, L2 learners with higher English proficiency tend to use more indirect request strategies, but they have not developed pragmatic competence to adjust their usage across written contexts. Findings are discussed in relation to pedagogical implications for developing writing competence of L2 learners, which should be attuned to diverse rhetorical expectations and individual needs.