Users and organizations alike continue to make the same mistakes and use the same unreliable technologies and practices I’ve been immersed in IT security for more than two decades, and I’ve learned a lot along the way. Yet for all the knowledge I’ve soaked up, several questions still baffle me. Some of them pertain to end-users who seem to fall for the same sorts of scams year after year. Others, though, relate to security technologies and practices that organizations continually embrace, though they don’t work as well as they should — if at all.The following is just a short of list the questions that nag me day to day as I’m hunkered down in the IT security trenches.[ InfoWorld’s Malware Deep Dive special report tells you how to identify and stop online attacks. Download it today! | Roger A. Grimes offers a guided tour of the latest threats in InfoWorld’s Shop Talk video, “Fighting today’s malware.” | Stay up to date on the latest security developments with InfoWorld’s Security Central newsletter. ]How can people in this day and age readily send thousands of dollars to strangers for deals they already know are too good to be true?How come people believe every fake virus warning they see, yet not take the slightest precautions against real viruses?How come it took over a decade for DNSSEC to be approved — and why are organizations not implementing it?Why is it taking so long for IPv6 and its protections to be implemented?Why are we using perimeter firewalls when they don’t appear to stop hackers or malware, and instead just frustrate legitimate users?Why does my antispam service block some spam messages while letting other near-identical ones slip through?Why haven’t my multiple antispam services figured out that I don’t want to receive messages written in a language other than English?Why isn’t snopes.com on everyone’s favorites list, especially those who fall victim to hoax after hoax?Why does it seem like no young people care about privacy?Why don’t most companies teach their end-users about the latest threats, such as fake antivirus warnings, advanced persistent threats, and so on?Why does almost every company fail to perform basic patching?Why is it easier to teach 3-year-olds about computers than 70-year olds?Why are we still living with inaccurate antivirus scanning programs 20 years later?Why are popular mobile app stores full of malware in today’s day and age?Why are we inventing new protocols and services that don’t have security ingrained from the very beginning?Why do the security questions that supposedly protect your password require information that can easily be gleaned off the Internet?Why do some CEOs still think that advanced persistent threats are overhyped until it’s shown their organizations have been compromised for years?Why don’t all computer apps automatically and invisibly patch themselves?Why are computer users more likely to be dupedy by malware and scammers today than 10 years ago?In truth, I know the answers to most of these question — which makes it more frustrating that we still have to ask them. What computer security questions do you still ponder? This story, “The 19 most maddening security questions,” was originally published at InfoWorld.com. Keep up on the latest developments in network security and read more of Roger Grimes’s Security Adviser blog at InfoWorld.com. For the latest business technology news, follow InfoWorld.com on Twitter. Related content analysis The 5 types of cyber attack you're most likely to face Don't be distracted by the exploit of the week. Invest your time and money defending against the threats you're apt to confront By Roger Grimes Aug 21, 2017 7 mins Phishing Malware Social Engineering analysis 'Jump boxes' and SAWs improve security, if you set them up right Organizations consistently and reliably using one or both of these approaches have far less risk than those that do not. By Roger Grimes Jul 26, 2017 13 mins Authentication Access Control Data and Information Security analysis Attention, 'red team' hackers: Stay on target You hire elite hackers to break your defenses and expose vulnerabilities -- not to be distracted by the pursuit of obscure flaws By Roger Grimes Dec 08, 2015 4 mins Hacking Data and Information Security Network Security analysis 4 do's and don'ts for safer holiday computing It's the season for scams, hacks, and malware attacks. But contrary to what you've heard, you can avoid being a victim pretty easily By Roger Grimes Dec 01, 2015 4 mins Phishing Malware Patch Management Software Podcasts Videos Resources Events SUBSCRIBE TO OUR NEWSLETTER From our editors straight to your inbox Get started by entering your email address below. Please enter a valid email address Subscribe