Almost every day, there’s news about a massive data leak -- a breach at Yahoo that reveals millions of user accounts, a compromise involving Gmail phishing scams. Security professionals are constantly moving the chess pieces around, but it can be a losing battle.

Yet, there is one ally that has emerged in recent years. Artificial intelligence can stay vigilant at all times, looking for patterns in behavior and alerting you to a new threat.

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Want to make a cool $20,000?

All you have to do is hack the Nintendo 3DS, a handheld console that’s been out for a few years already. A listing on HackerOne spells everything out: Hackers will receive a cash payment for discovering a vulnerability in the system, which does let gamers make purchases and stores private information like your age and gender. There’s a range for this, of course -- some discoveries will pay $100. Also, anyone who files a report must follow the exact template.

It makes you wonder -- why would a major Japanese corporation offer a reward like this? Why is it even worth the expense, especially when you know they have internal security researchers?

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A product marketing manager at your company just posted a photo on LinkedIn. The problem? In the background of the image, there’s a Post-It note that contains his network passwords. You can barely see it, but using artificial intelligence algorithms, hackers can scan for the publicly available image, determine there are network passwords, and use them for data theft.

According to data security expert David Maynor, this is not rocket science. In fact, the AI program is easier to use than a search engine. “The AI can identify objects in an image and the environment of the photo, guess at a description of the image contents as well as your likely age, gender, facial expression, and more,” says Maynor. “And these tools are becoming increasingly powerful with every image they scan, learning and becoming more accurate.”

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Wait, what?

If this rumor about Verizon buying Yahoo for $5B is true, we have an honest to goodness schadenfreude moment for me as someone who remembers the days of the Buddy List, giant banner ads (which is actually still common at Yahoo Mail for some reason), and those plastic discs they might still sell at Walmart for gaining “high-speed Internet” access.

As you may know, Verizon also owns AOL. Those three letters, combined with the Yahoo exclamation mark, create some vivid memories. Few of them are good ones. I remember having to wait for my modem to connect to AOL back in the day, and for the banner ads at Yahoo.com to finish loading. It’s a curious development, but it makes about as much sense as other luminous icons of tech combining into an ungodly entity driven by brand dominance.

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If you're looking for a good lesson in enterprise security, there might be a few sitting in the parking lot. The automotive field is a glaring example of "worst practices" in security, say several automotive experts. And, the problem is only getting worse, not better.

Over the past few years, the cars have come under fire for many things -- constant recalls, safety hazards, and diesel-engine tricks to name a few-- but security experts have noticed a disturbing trend.

While it might be hard to break into a BMW unless you have a rock handy, there hasn't been as much effort in protecting wireless signals, establishing standards, creating new regulations and laws, and patching much more aggressively.

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The burgeoning market for gadgets that trigger a sprinkler system, help you count the number of times you swing a bat, or dim the lights automatically are rising.

That’s a concern for any business due to how these devices are also starting to show up at the corporate office for use in conference rooms, executive suites, and even as a low-cost building security camera system. Experts claim the industry is not doing enough to protect these devices.

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People who lead large IT organizations don’t have much time to deal with the nitty-gritty technical details of how their systems run. Their priorities are to provide strategic technology leadership, set policies and manage the overall operation. CIOs and other IT leaders also have to work with executives in other departments to make sure IT is providing the services the business needs. But there are times when a technical problem crops up that requires the boss’s attention, and on those occasions finding the right solution can seem like an overwhelming challenge.

To get a sense of the type of technical issues CIOs have to deal with, we asked five IT leaders to recall vexing problems they were able to solve without resorting to complicated, high-cost rollouts.

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What is a ‘fringe’ device in IT?

For some, it’s a gadget everyone has forgotten about — a printer in a corner office, an Android tablet in a public area used to schedule conference rooms. A fringe device can also be one that’s common enough to be used in the office yet not so common that everyone is carrying one around or has one hooked up to the Wi-Fi every day.

As with any security concern, many of these devices are overlooked. There might be security policies and software used to track and monitor iPads and Dell laptops, but what about the old HP printer used at the receptionist’s desk? In a hospital, it might be a patient monitoring device. In a more technical shop, it could be a new smartphone running an alternate operating system.

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