Recently, piracy emerged as the biggest obstacle confronting legitimate online music providers. To encourage customers to purchase music from authorised online sources, both antipirating and retention strategies must be effectively implemented. This study provides four generic retention strategies to encourage the purchase of legitimate online music: value-added product, low-price, legal action and technological protection. This paper also classifies online music users into two segments, legal and file-sharing, to provide additional managerial insights. This study proposes that value-added product, low-price, legal action and technological protection strategies all improve purchase intentions of legitimate online music. The value-added product and low-price strategy, which establish customers' attitudinal and behavioural loyalty, are more effective on file-sharing users than legal users. Both legal action and technological protection strategies, which create barriers and penalties for customer switching, have far greater impact on customer purchase intentions of legal users than file-sharing users.