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Trust and Technology: Important Considerations for the AI Era

Sherrod DeGrippo talks about trust and technology and the impact of AI.

Most of us use various kinds of technology all day, every day. But we don’t often think about what goes on behind the screens. We trust devices with years-outdated security, depend on systems very few people actually understand, and now turn to AI for all kinds of questions without really knowing how these systems work. Modern technology brings convenience, but it comes with tradeoffs. Trust and technology are key considerations in our ever-advancing tech-driven world.


See When Trust Becomes a Trap with Sherrod DeGrippo for a complete transcript of the Easy Prey podcast episode.

Sherrod DeGrippo has been in information security and threat intelligence for over two decades. She current leads threat intelligence for Unit 42 at Palo Alto Networks, where she oversees teams that identify and respond to complex cyber threats. In her security career, she has worked at Nexum, Symantec, SecureWorks, and the National Nuclear Security Administration, and been in senior leadership roles at Microsoft and Proofpoint. The United Cybersecurity Alliance named her Cybersecurity Woman of the Year in 2022. She is also the author of Threat Driven Software Development: Defending Modern Online Services.

The Evolution of Technology

Sherrod got her first computer pretty young, and became fascinated with security the first time she popped a shell. An online friend showed her how to do a buffer overflow and get onto his computer. She was hooked – and drawn to making sure the wrong people couldn’t do those kinds of things.

Her first job in tech was with AT&T, where she did database repair. She had a lineman’s handset, and did what’s called beige boxing – opening up the big panels near the street, clipping in, and getting the line of any phone. A lot of the times those boxes weren’t secured at all. It let her get unlimited calls as a teenager, which wasn’t the best thing to be doing, but it was a different time. These days, kids aren’t experimenting with those kinds of things as much.

Sherrod’s generation was big on tinkering – they would open up devices to see how they worked and change them. But not many people do that anymore, especially not with TVs or mobile devices. You can’t even open most mobile devices without damaging them. We’re getting to a point where consumer devices really are consumer, and people who actually understand the technology and how it works are becoming rare.

We’re moving into this place where consumer electronics really are consumer. … That is going to make technologists, true technologists that understand how the systems work, more rare.

Sherrod DeGrippo

Some people still do understand the technology and build their own machines, but they’re the minority. These days, kids don’t learn how the tech works because they don’t need to. They trust that the technology works and it does. Those who do know how it works are going to be the last standard-bearers of how the world moves into the future.

The Existential Question of Automation

Sherrod sometimes wrestles with the existential question of if even people who make the technology won’t really understand how it works because of automation and AI involved in the process. She worries that we’re automating to the point of ignorance and lack of context, and that we’re eventually not going to have the knowledge we need. Think about older programming languages like COBOL and FORTRAN. A lot of systems still require them. But most of the people who built and designed these systems have retired or died. Where are the experts who can work on these systems? We’re running out of them.

A lot of this applies to networking, too. Hacker and phreaker types like Sherrod used to be constantly working with and thinking about where packets are going. If you type something into a computer, where does it end up and how does it get back to you? But a lot of that isn’t really something even technologists have to deal with anymore.

The other side is the amount of traffic that’s going to and from our devices all the time. Sometimes people will download something like Wireshark, see all this traffic going through their device, and assume they’ve been hacked. But it’s all normal. Even if it’s just things like your Microsoft Office checking for an update, our devices are sending and receiving things constantly, even when you’re not using it. Most of us trust the technology without really being aware of what’s going on behind it.

The Risks Hiding in Home Technology

Many consumers don’t think about their home routers very much. Chances are good that your cable company or ISP provided the device and as long as it works, nobody thinks about it once it’s set up. So it’s probably pretty old – and if the company ever provided firmware updates, they probably stopped less than a year after you got it. So many homes have unmonitored and outdated devices running their home internet, and it’s not even their fault. People don’t even realize they shouldn’t trust this older technology.

Foreign actors like Russia and China use American home routers to launch attacks. They do it because it looks like they’re coming from a standard home IP address, and because most routers never get updated. They’re in people’s homes, but because the ISP provided it, people don’t feel responsible for it. Even if you did try to update your router, chances are good that there aren’t any updates available because the device is too old.

Unfortunately, this is an issue that spans the whole world. There are a lot of vulnerable devices in homes and small offices, and threat actors are using that. It’s something that keeps Sherrod up at night. Our global networks are surprisingly frail. We depend on protocol-level services, and she worries about how they’re being maintained and whether they’re resilient.

The fragility of the global network and its security makes me nervous.

Sherrod DeGrippo

How AI Could Undermine Humanity

One major thing that Sherrod is very concerned about is AI – and not in the way that you think. Lots of people say that AI is going to destroy humans, and she doesn’t think there’s a risk of AI setting off a huge firebomb or killing us all. But she worries about us losing our humanity by replacing human connection with AI.

I think the biggest risk to humanity today with this is the severing of human connection in preference to an AI.

Sherrod DeGrippo

As a personal example, Sherrod’s personal trainer moved away, so she decided she needed to figure it out on her own. Her first thought was to get on ChatGPT, tell it her goals, and have it put together a workout plan for her. But she had another option. She has plenty of friends who are “gym nerds” and really into fitness. Ultimately, she chose to talk to her friends, and she’s glad she did. It look longer and they had their own opinions, but the result was good and she was happy to choose connection.

She worries people will not have that level of thought and mindfulness and just go to AI instead of other people. People are already drawn to the lowered friction of AI. But friction is what leads to intimacy, connection, and depths in relationships. It’s a foundational part of the human experience. If we choose a lack of friction over the friction that leads to connecting with each other, it will erode our relationships. Sherrod sees the potential for AI to destroy humanity by cutting us out of relationships.

Friction is a foundational part of the human experience … I do worry that there is the potential for AI to destroy humanity by cutting us out of relationships.

Sherrod DeGrippo

The Limitations of AI Technology

We’re already seeing a lot of people ask their medical question to AI instead of their doctor, or asking it relationship questions or about how to manage a team. They’re taking these very human questions to a computer that summarizes information that may or may not be good and tells them how to form or maintain human connection.

AI is a major factor in trust and technology.

If you get on your phone and type in a word, it’ll give a list of potential autocomplete options. When this feature first came out, people would just tap options and make a crazy nonsense sentence. In many ways, this is what generative AI is doing today. It’s like a much more sophisticated auto-complete that predicts what the next word in a sentence would mostly be. AI predicts what the answer most commonly is and give it to you, with no idea of whether it’s right or useful to you.

You also can’t get true creativity or innovation from something that’s trained on past knowledge. At the level this tech is at now, it can’t synthesize or develop new ideas. Especially when the question is about human relationships, you shouldn’t necessarily trust AI technology. If you want a better social life, talk to your friend. If you want to lead your team at work better, find a leader who’s doing a great job with their team and ask them how they’re doing it.

AI is great for organizing schedules and doing similar low-grade and annoying labor. But if you want real human connection, you have to talk to humans. It’s hard to make friends as an adult, and it’s even harder if you’re talking to an AI instead of a person.

Don’t Let AI Run Your Life

AI has some incredible capabilities, and Sherrod does think it can do a lot for us. But we have to assert our humanity when using it. You’re not going to have a great experience if you’re just sitting back and letting life happen to you. To be fulfilled, happy, and satisfied, you have to make your own decisions.

To be fulfilled and happy and satisfied and content and successful in life, you have to get in your own driver’s seat. You have to make the decisions.

Sherrod DeGrippo

Trip planning is a great example. AI is great for logistics stuff. You can say “I want to do these things on the same day, how should I arrange my schedule,” and that’s great. But you need to decide what you want to do and how you want to feel on this trip, or it’s not going to be as much fun. Any time you let another force, whether that’s your family, your significant other, society, or an AI, dictate what you experience, you’re not going to be happy.

Life has to be intentional. And the more friction you eliminate in your life, the fewer choices you have, the fewer feelings you experience, and the fewer interactions you need to (and get to) have with others. That’s not a human life. AI’s great benefit is it lets you decide where you want that friction. Sherrod is a computer nerd, but she optimizes for how something makes her feel. She doesn’t want AI to optimize away the things she wants out of her life.

The more you eliminate friction from your life, the less choices you have to make, the less feelings you have to process, the less interactions you need to have with other humans, that’s not a human existence.

Sherrod DeGrippo

AI Technology Makes it Easier to Trust Scammers

Another element of AI that concerns Sherrod is that it’s eliminating human want and desire. Because AI can get you pretty much anything you want almost immediately, people don’t have to sit with desires, understand complexity, or deal with the complications of what it feels like to want. And this is part of why scams and fraud are so successful these days.

Sherrod always reminds people that social engineering is key. It’s getting someone to do something you want that they wouldn’t have done otherwise. These concepts are thousands of years old. People have been stealing, gathering info, and social engineering since the beginning of human society. Today they do it with computers and technology, but the goal isn’t any different. It’s still financial gain or getting information (also for financial gain).

Since organizational human society, we’ve been doing [crime]. Today, the people doing them use computers and technology. And the goal isn’t different.

Sherrod DeGrippo

We call some types of computer viruses “Trojans” after the original Trojan horse, which was made of wood. These tactics aren’t new. But our desire for a frictionless society makes it worse. The path of least resistance is often a scam. Asking questions, slowing down, and being secure is friction. Defending a network introduces friction. But scammers and hackers are very good at making the things they want you to do frictionless. They implement technology to make you want to trust them because it’s just easier. Being secure is harder.

The Upsides of AI

AI isn’t all doom and gloom, though. Sherrod thinks there will be changes as AI affects how things function, but that makes it possible to make things more human focused. Spending time understanding consumers and how they make decisions puts humans back in the loop.

Lots of people say AI won’t take blue-collar jobs, and Sherrod thinks that’s not quite true. She lives in a lovely old house built in the 1950s, and last winter the HVAC system went out. It was freezing cold, and none of the companies she called could get someone out sooner than in four days. It was so cold that Sherrod decided to see if there was anything she could do about it. In the basement, she found the original manual for the furnace. She took it upstairs, scanned it on her phone, uploaded it to ChatGPT, and asked it what to do. With the manual and pictures of her furnace, it walked her through a fix. She got her heat back on.

AI isn’t going to be able to install furnaces or actually come out and do the work. But it can eliminate that initial diagnostic call. Many people are going to be able to figure it out themselves with AI help, especially for people who are in trouble. It puts consumers in a really strong situation when they can trust AI technology to give them basic information.

AI Brings New Possibilities

One important caveat when it comes to AI is that it’s not an expert in anything. Go talk to any AI about your area of expertise and you’ll quickly find out it only has the basics. But when you can be basic at anything, you can get a lot done. You’re not an expert because you have ChatGPT, but you can get a basic understanding. And generalists can make a lot happen.

Don’t fool yourself into thinking you’re an expert just because you have ChatGPT. You’re not. But you could get basic.

Sherrod DeGrippo

If you like cooking and cleaning but hate planning what you’re going to eat, you can put recipes you like into ChatGPT and ask it to plan out your meals for a month. It takes time to get that set up, but once it’s set up, you can offload tasks you hate. Extrapolating further, there are now plugins that will let the AI order your groceries for the week based on your meal plan, too.

It can also provide opportunities for connection if you use it right. One suggestion Sherrod has given before is to have ChatGPT plan an entire party, then invite people to find out how an AI-planned party goes. Use it as a reason to get together. You don’t have to trust the technology with all aspects of your life. Use it to get rid of the things you don’t enjoy and facilitate the things you do. If you’re not being intentional about what you offload, you’ll end up in a horrible reality where you’re not connecting with other humans anymore.

Connect with Sherrod DeGrippo on LinkedIn. Find her new book, Threat Driven Software Development: Defending Modern Online Services wherever books are sold.

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