From Monoliths to Swarms: A Study of Attack Surface Evolution in the Transition to Multi-Agent Web Systems

Large Language Model (LLM)-based web agents are increasingly evolving from single-agent systems (SAS) to multi-agent systems (MAS). While MAS can lead to improved task performance by decomposing complex tasks across specialized sub-agents, such role decomposition introduces new structural attack surfaces that are absent in SAS. This expanded attack surface remains poorly understood and inadequately categorized. To address this, we propose a taxonomy to categorize attack vectors specific to web-based MAS, accounting for vulnerabilities introduced or amplified by the involvement of multiple agents. We further present a test-bed WebMASLab to analyze web agent security against a fully external, web-only adversary. To isolate the effect of architecture, we keep the user task, tool surface, and browser substrate fixed, and compare single- and multi-agent setups. We evaluate three adversarial scenarios, across three conditions (baseline, prompt-hardened, and reasoning-enabled), including a novel MAS-specific Telephone Loop attack that exploits cross-agent delegation to create cyclical task loops. The attack is inert against SAS but compromises MAS when powered by three of the four frontier models evaluated (Claude Sonnet 4.5, GPT-5.2, GPT-5.4), averaging 80% across them at baseline. Only the fourth model, Claude Sonnet 4.6, resists the attack with a 92% detection rate. For the rest, the detection is 0% at baseline, reaching 33% with prompt-hardening for one model. We also show that obvious defenses do not generalize; prompt-hardening collapses one model's ASR from 100% to 8% while providing only modest reduction to the others. Our findings demonstrate that the transition from single- to multi-agent web systems changes the security landscape. Role specialization may not only lead to performance optimization but also introduce new architectural risks that require further study and defenses.