Dynamic Searchable Symmetric Encryption (DSSE) allows secure searches over a dynamic encrypted database but suffers from inherent information leakage. Existing passive attacks against DSSE rely on persistent leakage monitoring to infer leakage patterns, whereas this work targets intermittent observation - a more practical threat model. We propose Peekaboo - a new universal attack framework - and the core design relies on inferring the search pattern and further combining it with auxiliary knowledge and other leakage. We instantiate Peekaboo over the SOTA attacks, Sap (USENIX' 21) and Jigsaw (USENIX' 24), to derive their “+” variants (Sap+ and Jigsaw+). Extensive experiments demonstrate that our design achieves >0.9 adjusted rand index for search pattern recovery and ~90% query accuracy vs. FMA's ~30% (CCS' 23). Peekaboo's accuracy scales with observation rounds and the number of observed queries but also it resists SOTA countermeasures, with >40% accuracy against file size padding and >80% against obfuscation.

Searchable symmetric encryption schemes often unintentionally disclose certain sensitive information, such as access, volume, and search patterns. Attackers can exploit such leakages and other available knowledge related to the user's database to recover queries. We find that the effectiveness of query recovery attacks depends on the volume/frequency distribution of keywords. Queries containing keywords with high volumes/frequencies are more susceptible to recovery, even when countermeasures are implemented. Attackers can also effectively leverage these “special” queries to recover all others. By exploiting the above finding, we propose a Jigsaw attack that begins by accurately identifying and recovering those distinctive queries. Leveraging the volume, frequency, and co-occurrence information, our attack achieves 90% accuracy in three tested datasets, which is comparable to previous attacks (Oya et al., USENIX' 22 and Damie et al., USENIX' 21). With the same runtime, our attack demonstrates an advantage over the attack proposed by Oya et al (approximately 15% more accuracy when the keyword universe size is 15k). Furthermore, our proposed attack outperforms existing attacks against widely studied countermeasures, achieving roughly 60% and 85% accuracy against the padding and the obfuscation, respectively. In this context, with a large keyword universe (≥3k), it surpasses current state-of-the-art attacks by more than 20%.