This paper aims to evaluate the cyber security culture readiness of organizations from different countries and business domains when teleworking became a necessity due to the COVID-19 crisis We have designed a targeted questionnaire and conducted a web-based survey addressing employees while working from home during the COVID-19 spread over the globe The questionnaire contained no more than 23 questions and was available for almost a month, from 7th April 2020 until 3rd May 2020 During that period, 264 participants from 13 European countries spent approximately 8 minutes to answer it Gathered data were analyzed from different perspectives leading to evolutionary findings regarding information security readiness and resilience of both individuals and organizations In this paper, results are being presented and discussed in detail while focusing on future scientific routes and research paths that need to be explored It concludes on a number of cyber security recommendations addressing both the emerged vulnerabilities and the need for security culture evolution © 2021, The Author(s), under exclusive licence to Springer Nature Limited part of Springer Nature