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Abstract:Decisions regarding information system evolution strategy become topical as the organisation's information systems age and start to approach the end of their life cycle. An interview study was conducted in order to compare factors influencing modernisation and replacement initiation. System age, obsolete technology and high operation or maintenance costs were identified as triggers for both modernisation and replacement projects. The results show that the most prevalent individual reason for modernisation initiative is business development. Common initiation factors for replacement projects were end of vendor support and system's inability to respond to organisation's business needs.