L'histore se répète. In general, each development wave of new technology shows a lack of security. The same lack of security can be found in the area of information and communications technology resulting in a lack of Critical Information Infrastructure (CII) Assurance. By looking back, we can predict the upcoming operational and maintenance issues in critical information infrastructure assurance. Organisational, manufacturing, awareness, educational, and technical threats and related information assurance gaps can be predicted. What are the information assurance challenges to avoid a failure of the CII?