Analysis Of Forensic Readiness And Chain Of Custody For Ai-Assisted Cybercrime Evidence

06 Oct 2025 --
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1. United States v. Lori Drew (2008)

Background:
Lori Drew was involved in a cyberbullying case using automated bots and AI-like systems to interact with the victim online. The case raised significant questions about digital evidence handling, particularly regarding automated accounts and logging systems.

Forensic Readiness:

Investigators collected computer logs, email headers, and social media server data.

Forensic tools were used to preserve the integrity of digital evidence before analysis.

Chain of Custody Issues:

Defense argued that server logs could have been altered, raising challenges regarding whether evidence had been tampered with during collection.

Court emphasized proper documentation of who accessed the servers, timestamps, and hash values to prove evidence integrity.

Outcome:

Drew was convicted of misdemeanor violations.

Highlighted the importance of forensic readiness—preparing systems and processes in advance to preserve AI-related evidence.

Significance:
Even early AI-assisted interactions required careful chain-of-custody documentation to ensure admissibility of evidence.

2. United States v. Michael Coscia (2015)

Background:
Michael Coscia used an AI algorithm for automated spoofing in commodity markets. The case involved the collection and analysis of algorithm logs and trading system data.

Forensic Readiness:

Investigators had to extract algorithmic trading records from proprietary trading systems.

AI-assisted financial fraud required specialized forensic tools to interpret automated decisions and trading patterns.

Chain of Custody Issues:

Logs were exported and hashed immediately to preserve integrity.

Multiple copies were maintained with strict access control to prevent tampering.

Court required forensic documentation linking the algorithm’s execution to Coscia’s actions.

Outcome:

Coscia was convicted of commodities fraud and spoofing.

Evidence from automated systems was admitted because of careful preservation and documented chain of custody.

Significance:
Demonstrates that AI systems themselves can be treated as evidence sources, but forensic readiness is critical to establish authenticity.

3. United States v. Aaron Swartz (2011–2013)

Background:
Aaron Swartz used automated scripts to download academic journal data from JSTOR. While not strictly AI, autonomous systems were used to access and move large datasets.

Forensic Readiness:

Investigators seized servers, hard drives, and access logs.

Digital forensics tools were applied to reconstruct the sequence of automated requests and downloads.

Chain of Custody Issues:

Chain of custody included seizure of physical hardware and digital images.

Forensic experts documented timestamps, MD5 checksums, and storage environments to preserve evidence authenticity.

Outcome:

Swartz faced federal charges; case settled tragically with his death.

Highlights the challenges of ensuring AI/automation-driven actions are fully traceable in forensic analysis.

Significance:
The case illustrates that evidence from autonomous or semi-autonomous systems must be captured with forensic readiness in mind to establish integrity and prevent challenges in court.

4. United States v. Ulbricht (Silk Road Case, 2015)

Background:
Ross Ulbricht operated the Silk Road dark web marketplace, which used automated scripts, bots, and AI-assisted systems for transactions and anonymity.

Forensic Readiness:

Digital evidence included server logs, cryptocurrency blockchain records, and automated marketplace scripts.

Forensic teams prepared imaging and hashing procedures to preserve evidence integrity.

Chain of Custody Issues:

Evidence was collected from multiple jurisdictions, requiring careful documentation of seizure, storage, and transport.

Experts presented detailed timelines showing how AI-assisted scripts linked Ulbricht to criminal transactions.

Outcome:

Ulbricht was convicted on multiple counts including money laundering and drug trafficking.

Evidence derived from AI-assisted systems was central to the prosecution.

Significance:
Shows the necessity of international forensic readiness and strict chain-of-custody procedures when AI-assisted systems are involved.

5. United States v. Robert Hepting (2006)

Background:
Robert Hepting was charged with unauthorized access and distribution of telecommunications data using automated scanning and AI-assisted analysis tools.

Forensic Readiness:

Investigators captured automated system logs and analyzed AI-assisted intrusion attempts.

Data preservation plans were in place to prevent corruption or loss of automated activity records.

Chain of Custody Issues:

Logs from multiple servers were timestamped and hashed.

Multiple forensic copies were maintained to allow validation in court.

Defense raised concerns about possible alteration of automated logs, but proper forensic documentation overcame this challenge.

Outcome:

Hepting settled civilly, with criminal charges dropped, but case reinforced importance of maintaining chain of custody for AI-assisted cybercrime evidence.

Significance:
Highlights that automated tools produce complex datasets requiring rigorous forensic readiness and well-documented custody procedures to ensure admissibility.