This time of year is traditionally for either looking back at the previous year or looking forward to the year ahead. While there have been great advances over the years with respect to information security tools, technologies, training and awareness, significant challenges remain. What follows are my estimations of the top information security challenges for 2022. Please note that I could probably have written the same challenges for 2021, 2019, 2001 and perhaps even 1973. Some of these issues are perennial, some are new. And as a lawyer, some of these challenges are specific to security-focused lawyers rather than technical challenges which might be faced by CISOs.