Personalized AI assistants, a hallmark of the human-like capabilities of Large Language Models (LLMs), are a challenging application that intertwines multiple problems in LLM research. Despite the growing interest in the development of personalized assistants, the lack of an open-source conversational dataset tailored for personalization remains a significant obstacle for researchers in the field. To address this research gap, we introduce HiCUPID, a new benchmark to probe and unleash the potential of LLMs to deliver personalized responses. Alongside a conversational dataset, HiCUPID provides a Llama-3.2-based automated evaluation model whose assessment closely mirrors human preferences. We release our dataset, evaluation model, and code at https://github.com/12kimih/HiCUPID.

Recent advancements in multi-turn voice interaction models have improved user-model communication. However, while closed-source models effectively retain and recall past utterances, whether open-source models share this ability remains unexplored. To fill this gap, we systematically evaluate how well open-source interaction models utilize past utterances using ContextDialog, a benchmark we proposed for this purpose. Our findings show that speech-based models have more difficulty than text-based ones, especially when recalling information conveyed in speech, and even with retrieval-augmented generation, models still struggle with questions about past utterances. These insights highlight key limitations in open-source models and suggest ways to improve memory retention and retrieval robustness.