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📄 Abstract
Abstract: With the increasing use of conversational AI systems, there is growing
concern over privacy leaks, especially when users share sensitive personal data
in interactions with Large Language Models (LLMs). Conversations shared with
these models may contain Personally Identifiable Information (PII), which, if
exposed, could lead to security breaches or identity theft. To address this
challenge, we present the Local Optimizations for Pseudonymization with
Semantic Integrity Directed Entity Detection (LOPSIDED) framework, a
semantically-aware privacy agent designed to safeguard sensitive PII data when
using remote LLMs. Unlike prior work that often degrade response quality, our
approach dynamically replaces sensitive PII entities in user prompts with
semantically consistent pseudonyms, preserving the contextual integrity of
conversations. Once the model generates its response, the pseudonyms are
automatically depseudonymized, ensuring the user receives an accurate,
privacy-preserving output. We evaluate our approach using real-world
conversations sourced from ShareGPT, which we further augment and annotate to
assess whether named entities are contextually relevant to the model's
response. Our results show that LOPSIDED reduces semantic utility errors by a
factor of 5 compared to baseline techniques, all while enhancing privacy.
Authors (2)
Jayden Serenari
Stephen Lee
Submitted
October 30, 2025
Key Contributions
Introduces the LOPSIDED framework, a semantically-aware privacy agent that safeguards PII in LLM conversations by replacing it with semantically consistent pseudonyms. It preserves contextual integrity and depseudonymizes responses, unlike prior work that degrades quality.
Business Value
Enables the secure deployment of conversational AI in sensitive domains (e.g., healthcare, finance) by protecting user privacy, fostering trust and compliance with regulations like GDPR.