A Tangled Digital Web: Deception Versus the Modern Technology Stack

This column looks at how technology is transforming evidence, litigation, and dispute resolution. This installment looks at the technology stack and what it means for deception. Past editions of the column can be found here .

“Oh, what a tangled web we weave, when we practice to deceive.”—Sir Walter Scott

Over two hundred years ago, Sir Walter Scott warned us that deception creates a tangled web. Today, that warning feels less like poetry, and more like a description of how our systems actually work. For years, people who wanted to hide digital misconduct often thought about evidence too simply: delete the email, rename the file, wipe the USB history, clear the obvious trace, and move on. That logic belonged to a world in which evidence appeared to live in fewer places, and the act itself seemed narrow enough to clean up. If the file was gone, the story was gone. If the message disappeared, the risk disappeared with it.

But the modern user no longer lives in that simpler world. A single act can now leave traces in more places than most people realize. This includes on the device, the operating system, in application logs, in indexes, across sync folders, and inside cloud platforms. This also includes backup systems, mobile phones, collaboration tools, network infrastructure, and third-party records the actor may know about but cannot access or alter.

The full set of hardware, software, systems, and services engaged when someone performs a digital act is known as their “technology stack.” Even a simple email can touch far more than the user realizes: the device, the operating system, the email application, local network services, authentication layers, the domain server, cloud infrastructure, and downstream storage. On an even more granular level, it may also involve the keyboard, hard drive, display, spell check, caches, indexes, and increasingly embedded AI tools such as Copilot. And that is still only an abbreviated list.

The ordinary technology stack is now layered and distributed, and even a simple act can create side effects in places the user never thinks to check. The actor who tries to hide one event is often forced to chase its echoes across systems they do not fully understand.

That is why concealment has become so difficult. Not impossible, but more challenging than people expect. The obvious artifacts may be erased while the surrounding traces remain. A file may be replaced while the index still remembers it. A thumb drive may be removed, but the operating system, file system artifacts, or other secondary records continue to show that it was used.

Concealment as evidence

In many cases, concealment creates new evidence rather than eliminating old evidence. And that is the reality of modern digital investigations: as the technology stack becomes more complicated, the effort to deceive often becomes easier to detect.

We are now seeing this in the courts. In one recent matter, an actor replaced a file on a computer with an alternative version and then took steps to erase the traces of that replacement. But the effort was incomplete. The actor failed to identify and remove all instances where the thumb drive activity, file changes, and the system’s awareness of the file had been recorded. As a result, we were able to do more than show that the file had been replaced. We were able to show that someone tried to hide it. That distinction matters. It shifts the issue from a technical anomaly to a question of intent.

Complexity can make systems harder for ordinary users to understand, but it often makes conducting tests easier. Every new layer in the stack is another possible witness. Some witnesses are noisy. Some are partial. Some require interpretation. But together they can tell a story that is much harder to rewrite after the fact.

The asymmetry issue

There is another important wrinkle. Not every relevant data source is under the actor’s control. A person may know their phone location was recorded by a carrier signal tower. They may know a cloud provider logged their IP address. They may know a third-party system captured a transaction. But knowing that a record exists is not the same as being able to alter it. That asymmetry is enormously important in investigations and litigation. Some of the best records are the ones outside the reach of the person with the greatest incentive to change the story.

This is why digital evidence work increasingly requires a broader view than simply asking whether a file exists or a message was sent. The better question is: what would this activity have touched? What systems should have noticed it? What traces would normally be created? And which of those traces are present, absent, inconsistent, or impossible to reconcile? 

A guide to reenactment

In fact, one of the best techniques in conducting these investigations is to virtually re-enact the day in question to understand what actions the parties might have taken and, hence, where to look. Modern evidentiary work is less about finding one magic artifact and more about testing a claimed reality against the full stack of available signals.

That is how we think about inspections. We look through four panels:

1. What is there that should be there?
2. What is there that should not be there? 
3. What is not there that should not be there?  
4. What is not there that should be there? 

Those four views help turn technical clutter into evidentiary meaning. They let us see not only what happened, but sometimes what someone hoped we would never see.

The irony is that the digital world has become more complex, but many cases are easier to test. Not easier because the facts are simple. Easier because deception now has more surfaces to manage, more systems to outsmart, and more chances to fail. In a layered environment, the tangle is already there. The person trying to deceive is not building it from scratch. They are getting caught in it.

Sir Walter Scott described the problem as a tangled web. What he could not have seen was how literal that web would become. In the modern technology stack, deception does not just create risk. It creates residue.

Join the conversation

This is just one piece of the bigger conversation on the future of evidence. As legal professionals, we need to stay on top of emerging technologies.

Let’s continue the discussion on this LinkedIn post.