arXiv:2607.21951v4 Announce Type: replace-cross Abstract: This paper investigates the adversarial manipulation of the ranked recommendations produced by web-augmented large language models (LLMs). When an LLM answers a recommendation query by retrieving and reading live webpages, it acts as a recommender, and each retrieved page becomes a potential attack surface. Prior work has examined fabricated products, retrieval poisoning, and rank promotion. However, these studies do not compare how different edits to an already retrieved page change the model's final ranking while the surrounding source set remains unchanged. To address this gap, we propose SIREN, an automated attacker--judge method that adapts the PAIR jailbreaking loop to competitive rank manipulation, with the goal of moving a chosen entity to rank~1 in an LLM-generated recommendation. SIREN retrieves and captures webpages using Anthropic's web tools, then iteratively edits a retrieved source using an interpretable taxonomy of 23 content-poisoning techniques. The custom-RAG replay platform keeps the same sources in the same order, so changes in the model's ranking can be linked to changes in the supplied content rather than to differences in retrieval. Across two production Claude models, SIREN reaches rank~1 in 62 of 124 technique trials nested within eight query--model contexts. The payloads that reached rank~1 were then tested in fresh sessions, where they reproduced the result with a mean success rate of 0.805. Across the evaluated settings, declarative ranking claims and seeded lists were generally more effective than directive-form injections, although the strength of this difference depended on the target model. To the best of our knowledge, this is among the first controlled studies of competitive rank manipulation in production LLMs where the supplied source context is kept fixed.