This chapter explores agile information practices of information systems development and argues that their history is much longer than what is generally believed today. We take an interpretive and critical view of the phenomenon. We made an empirical study of two companies that apply an XP-style development approach throughout the information systems development life cycle. The results of our research suggest that XP is a combination of best practices of traditional information systems development methods. It is hindered by its reliance on talented individuals, which makes its large-scale deployment as a general-purpose method difficult. We claim that XP can be useful for small colocated teams of skilled domain experts and implementers who are able to communicate well with the end users. However, these skilled and motivated individuals with high working morale can exhibit high productivity regardless of the methods used if they are not overly constrained by bureaucracy.