OSINT Rabbit Holes: When to Dig, When to Pivot, and When to Stop

Rabbit holes ARE inevitable

One search leads to a shell company. That shell company shares a nominee with three others. One is linked to a known proxy. There’s a leaked database. Then a Telegram channel. Then a football club in a sanctioned jurisdiction. Before you know it, you’re five pivots deep into something that looks explosive… but tells you nothing you can act on.

This is the OSINT paradox: the more you can find, the more disciplined you must become. There are three key points to keep front-of-mind when you’re drowning in possible avenues of investigation:

1. Not every trail is worth chasing.

2. Not every connection adds value.

3. Not every dead end is a failure.

Let’s explore why.

Why the Intelligence Cycle Still Matters

Too many analysts skip the foundational step: the requirement. We dive in, start pulling strings, and assume that something interesting will surface. But, OSINT is intelligence - and intelligence is a process.

This is where the intelligence cycle comes in. From direction to collection, processing to dissemination isn’t bureaucratic red tape. It’s your compass. It helps you frame the why? behind your investigation, keeps your outputs relevant, and ensures you’re not just collecting for curiosity’s sake.

When you’re in a rabbit hole, the intelligence cycle helps you stop and ask:

• Does this support the original objective?

• Am I answering the right question?

• Or have I started chasing what’s interesting rather than what’s useful?

By ensuring that you’re referring to the intelligence cycle throughout your investigation, you’re more likely to avoid going off-piste without realising.

Pivoting with Purpose

The power of OSINT lies in “pivots”, from one entity to the next, across data types, platforms and jurisdictions.

But here’s the truth: not all pivots are equal. A strong pivot is verifiable, contextually relevant and strengthens or refines your hypothesis. A weak pivot is coincidental, surface level (likes, follows, generic associations) and pulls you away from your original goal.

Tools like Videris (ok biased, shoot me……. please don’t, but I practice what I preach as we all should!) give investigators clarity. They surface pivots with context, timestamping, jurisdictional awareness, and risk indicators, all of which reduce the noise and help you decide early whether to dig deeper or stop.

Methodology Over Motion

The danger of rabbit holes is that they feel productive. But motion is not progress.

When you’re deep in a thread, ask yourself: Is this an investigative path or just movement? Am I collecting data I understand and can validate, or just stacking links?

Good tradecraft is about method, which should look something like this:

1. Build your hypothesis

2. Use tools to enrich and visualise

3. Test assumptions with multi-source corroboration

4. Capture every decision point so the path is explainable

5. Set thresholds for how far you’re willing to follow a thread

In short: don’t chase complexity for its own sake. You’re not trying to map the internet. You’re trying to deliver insight.

Knowing When You’re Stuck

Every investigator hits a wall sometimes. I’ve had personal experiences of this many a time, and heavy ones at that. Moving on……

Hitting a wall doesn’t mean you’ve failed, it might mean you’ve succeeded in exhausting what OSINT alone can give you (remember that OSINT is a discipline and what it can and can’t achieve).

Sometimes a dead end is the result. Other times, the lack of clarity is the finding: a nominee structure, a jurisdiction designed to hide data, a sudden drop in digital footprint after a key event. These are signals too.

When you keep digging past the point of relevance, you’re no longer investigating. You’re wandering. Instead, capture the dead ends and gaps, and share the path you took to get there. They’re part of the story, even if they don’t lead to a headline.

Reducing Noise, Amplifying Signal

We’re living in a very noisy OSINT landscape - from leaks, to scraped data, to AI-generated personas, false flags, and paid influence. With so much available, the challenge is not finding - it’s filtering.

This is where platform-enabled investigation changes the game.

Tools like Videris (there he goes again…...but hear me out) don’t just accelerate analysis. They prioritise:

• Signal over noise

• Entity resolution

• Risk-based filtering

• Human-led interpretation, powered by tech, (next bit is key) not replaced by it

In financial crime investigations, for example, where you’re tracking sanctions evasion, illicit flows, and proxies, these capabilities make the difference between direction and detour.

Be Willing to Walk Away

In OSINT, it’s easy to confuse depth with value - but the best analysts know when to stop.

Ask yourself:

• What requirement am I serving?

• Am I delivering insight—or just gathering information?

• Have I lost the thread, or found where it ends?

Sometimes walking away is the best decision you’ll make in an investigation. Remember that your job isn’t to know everything - it’s to know what matters, and why.

OSINT will always pull you toward the unknown. The question is: do you have the discipline to turn back?