Why OSINT Can Feel Stuck in the Stone Ages

Every time I start a new investigation, I feel like I'm transported back to 1955. OSINT software is still clunky, archaic, and hasn’t kept pace with what investigators actually need to do now. I don't believe it's just the platforms, though. Everyone's parroting the same footprint analysis steps while the people and companies we’re supposed to be tracking are essentially disappearing in plain sight.

Let me be clear: OSINT investigations today are maddening.

OSINT workflows haven’t budged

I don’t mean things like pulling email addresses, parsing domain ages, scraping social bios. I don't care about that. I’m talking about deeper things, like unspooling someone’s system, figuring out who they actually talk to, which companies they control, how they hide assets, where their proxies live, who launders what, and why a random tech consultancy in Moldova suddenly appears in five different registries.

It's always things like these that actually get investigators stuck. I remember spending 4 days on a corporate investigation when what I was looking for was scribbled in a Bengkulu business registry entry from 2010.

But many are still treating investigations like they’re collecting rare cards. “We found all their socials!” Great. Meanwhile the subject’s running seven identities across jurisdictions with mismatched transliteration conventions, and nobody even checked the Armenian tax portal because “we don’t usually look there.”

Recent investigation examples

1. The 2024 Vietnamese laundering network exploiting Singapore shell companies
Instead of focusing on the Instagram glamour, investigators cracked a US$8 million laundering operation by verifying nominee directors and shell company addresses lodged with Singapore’s ACRA, cross-referencing dissolved company addresses with regulatory postal code changes. This revealed the old identities of Vietnamese syndicate members.

2. The 2023-2024 Western Balkans cocaine smuggling ring‍

OSINT’s decisive clue came not from flashy cyber indicators, but Serbian and Montenegrin court archives detailing relationships of accused smugglers, indexed under maiden names predating digitized systems—showing how main actors shielded illicit finance through kinship-named logistics and proxy firms across the Balkans.

3. The Singaporean influencer scam operation (2023-2025)
The network wasn’t uncovered through “cyber indicators.” It blew open because someone finally bothered to examine the scanned Serbian court filings from 2016 that listed a cousin’s maiden name connected to a road haulage company. Nobody thought to look at pre-digitization archives. The entire network sat in a stack of PDFs that look like they were faxed through a meat grinder.

4. Bulgarian-Greek antiquities trafficking, 2024

A typo in a 2007 Bulgarian excavation permit surfaced alias usage by an art smuggling ringleader—this cross-referenced with current shipping manifests, OSINT social sleuthing of art sales, and trade data, helping connect identities in the renewed 2024 crackdown on Balkan trafficking in Greek artifacts.

And it goes on. And on. And on. Trust me, you don't want to see my notes.

Investigations are failing because they follow a stale structure

Honestly, you can predict the workflows for a simple POI investigation:

• Identify the subject.
• Collect their accounts.
• Pull their domains.
• Scrape public records.
• Repeat a little.
• Write a report.

It’s procedural and neat, but it's wrong for 2025.

Modern OSINT investigations require something closer to archaeology mixed with forensic linguistics. You need intuition about bizarre, random phenomena like naming conventions across cultures and murky offshore finance. Investigators need to know how paperwork actually gets filed in, say, the Philippines (where middle initials sometimes substitute for full names), or how Uzbek companies sometimes register foreign directors with date formats swapped depending on who typed it.

We don’t teach these things. We should. This is one of the largest areas, I believe, where AI can gather a corpus of domain-specific knowledge to aid investigators when they stumble across things like this.

Where OSINT investigations need to evolve immediately

1. Cross-jurisdiction identity variability
People forget that the same person’s name mutates differently depending on which registry clerk typed it.
Investigations need to incorporate phonetic, linguistic, and transliteration drift—Serbian Cyrillic, Armenian patronymics, Indonesian naming conventions, etc. Threat actors and criminals already exploit this; investigators need to catch up.

2. Long-tail registries
Everyone focuses on Delaware LLCs or UK Companies House, but navigating municipal registries in North Macedonia, or the Japanese gazette listings, or land records in Rajasthan that still store documents by family lineage is difficult.
Sometimes pretty important fragments hide there.

3. Secondary ecosystem mapping
Instead of looking at the target, look at the friend whose dog shows up in every background photo. Look at the sister-in-law’s suddenly international Etsy shop. Examine the procurement clerk's brother's fishing license.
Yes, these are real examples. I'm just remembering a Caucuses case where investigators mapped secondary actors and cross-checked licensing in the context of a 2024 procurement sanctions evasion case through obscure public records and non-obvious ties.

4. Public infrastructure footprints
Not in the cyber exposure sense, more like:

• What cell tower served their last known location?
• Which shipping manifests align with their travel?
• What municipal repair logs show when their street was last dug up, indicating new fiber installation?
  Little stuff. But this is where investigation gold lives.

5. Temporal patterns
Nobody timestamps anything properly. They just collect. But investigations hinge on sequences.
If a director resigns the same week a shipment diverts through a suspicious port, that matters.
If a domain updates its DNS records the same day a passport gets renewed? That matters too.

6. Non-digital crumbs
Newspaper clippings. NGO newsletters. Funeral announcements.
An art smuggling ringleader was identified once via a legacy shipping alias in scanned excavation permits, matched to exhibition catalogues published by accident.

Why this makes me more annoyed than I should be

It's because the gap isn’t funding. It isn't resources. It isn’t even skill (mostly).
It’s mindset and technology.

OSINT needs to stop behaving like a search engine and start behaving like a librarian who remembers which cousin married into which family in 2005.

Until OSINT investigators develop that instinct (messy, nonlinear, obsessive, forensic) people will keep slipping away behind new identities, new shells, new covers. And we’ll keep staring at the same dashboards, pretending the picture is complete.

It’s not. It never was (truly!).

But suppose we start looking in the places we’ve ignored. In that case, the dusty registries, the weird cultural naming quirks, the stray real-estate listings, the forgotten PDFs uploaded by mistake, actually surface in investigations.

Then maybe, we’ll stop running investigations like it’s 2016.

And start running them like it’s the world we actually live in now.