cs.CROct 24, 2026

Agent-to-Agent Synthetic Social Engineering on the Web

Authors: Bryan C. Boots

Organizations: University of Missouri-Kansas City, Kansas City, MO USA

Abstract

An AI agent can prepare an accurate report and still request an action its user has not authorized. Cooperation across Web services therefore requires separate judgments about identity, evidentiary support, and permission. We define synthetic social engineering (SSE) as deliberately deceptive or misleading influence intended to exploit AI recipients' responses to credibility, authority, or obligation cues and redirect behavior away from authorized objectives. We focus on separately tasked sender agents that produce or adapt misleading communication. Drawing on cybersecurity, social engineering, and persuasion research, we develop an operational framework connecting actors, deceptive representations, candidate influence routes, evidence or permission boundaries, responses, and consequences. The framework distinguishes attempts from successful redirection, without assuming human psychological processes. We implement it in the Agent Service Exchange and Evidence Commons (ASE-EC), a reproducible testbed with independently specified records and authorization scopes. Across 1,260 research episodes using Qwen3-4B in two fictional briefing tasks, matched comparisons test authority and commitment appeals, while defense comparisons assess protection alongside authorized task completion. Invoking a limited prior agreement increased unauthorized requests from 43.3% to 96.7%, although recipients retained supported decisions and permissions remained unchanged. These controlled findings identify action selection as a distinct security concern, even when evidence handling succeeds, and they provide a reusable basis for evaluating safeguards that preserve useful cooperation across Web services.

Explore similar work

Dec 29, 2025

It's a TRAP! Task-Redirecting Agent Persuasion Benchmark for Web Agents

Web-based agents powered by large language models are increasingly used for tasks such as email management or professional networking. Their reliance on dynamic web content, however, makes them vulnerable to prompt injection attacks: adversarial instructions hidden in interface elements that persuade the agent to divert from its original task. We introduce the Task-Redirecting Agent Persuasion Benchmark (TRAP), a benchmark for studying how persuasion techniques misguide autonomous web agents on realistic tasks. Across six frontier models, agents are susceptible to prompt injection in 25% of tasks on average (13% for GPT-5 to 43% for DeepSeek-R1), with small interface or contextual changes often doubling success rates and revealing systemic, psychologically driven vulnerabilities in web-based agents. We also provide a modular social-engineering injection framework with controlled experiments on high-fidelity website clones, allowing for further benchmark expansion.
May 14, 2026

The End of Trust: How Agentic AI Breaks Security Assumptions

For decades, the security of digital interaction has rested on an unacknowledged economic constraint. Attackers faced a tradeoff between the fidelity of a deception and the scale at which it could be deployed. Convincing impersonation required sustained human effort and was confined to a narrow set of high-value targets, while mass-market attacks sacrificed plausibility for reach. Detection systems, verification mechanisms, and user awareness training have all been implicitly calibrated to the artifacts of cheap deception that this tradeoff produced. Agentic AI collapses the tradeoff, allowing high-fidelity, individually tailored deception to be produced at mass-market scale. We argue that this shift exhausts a security paradigm rather than merely intensifying the threat landscape. We introduce the Infinite Impostor, an attack model in which an autonomous agent interposes itself between two parties who already trust each other, hijacking an existing relationship rather than building a new one from scratch. Detection-oriented defenses share an assumption that generative progress is eliminating, that synthetic outputs are distinguishable from authentic ones. We propose a suspect-by-default paradigm that shifts security from authenticating actors to evaluating actions, and examine the governance tensions that arise when platforms become the regulatory substrate of digital interaction.
May 30, 2026

"I Strongly Suspect This Website Is a Scam": Benchmarking PII Leakage and Detection without Defense in Autonomous Web Agents

Deceptive web content, widely instantiated across the internet and commonly known as social-engineering attacks, manipulates autonomous web agents into submitting users' personally identifiable information (PII) to attacker-controlled endpoints. In this paper, we show that social-engineering attacks are highly effective at extracting critical-tier PII from frontier web agents, posing a severe risk to deployed agentic systems. To quantify this risk, we introduce Scammer4U, a pre-registered benchmark of 91 attacker-controlled environments and 10 benign-twin baselines, spanning 8 attack vectors and 16 site categories on an 8-axis factorial taxonomy that isolates the causal contribution of individual attack design factors. Across frontier agents, we find that critical-tier PII leakage reaches 54--93% under no privacy guidance, compared to 0% on benign-twin baselines, confirming that leakage is attack-attributable rather than incidental form-filling. Escalating prompt-level mitigation yields sharply model-dependent reductions across the four families and remains insufficient to reliably prevent critical PII submission at the pooled level. Most critically, we identify a detection--action gap: agents whose reasoning an independent LLM judge confirms has flagged the site as suspicious still submit critical PII in 35.9% of sessions, versus 66.1% when no suspicion is verbalized, a 30.2% gap robust across all four model families. Our findings reveal that defenses conditioned on the agent's own recognition of an attack are gating on the wrong signal, motivating output-level interception of outbound submissions that operates independently of the agent's reasoning loop.