World media reports with appalling frequency on major information security incidents and data breaches. Some very recent announcements include meltdown and spectre vulnerabilities on global level as well as Swisscom announcing a data leak of 800’000 records of its customers on Swiss national level. These and other reported incidents had a very heavy impact on operation of businesses across the globe. As our lives become more and more digital with technologies such as Internet-of-Things being part of our day-to-day and blockchain systems providing a new roller-coaster for its users, we will try to follow in this talk the evolution of digital technology and connect it to related risks. This talk will try to explain why, even though some technologies become more mature and accessible, we still fail to bring the necessary information security and assurance to common users. The speaker will also try to bring forward some suggestions based on his own experience managing cybersecurity risk in large entities and smaller companies.