One of the most common, helpful practices of data scientists, when starting the exploration of a given dataset, is to examine existing data exploration notebooks prepared by other data analysts or scientists. These notebooks contain curated sessions of contextually-related query operations that together demonstrate interesting hypotheses and conjectures on the data. Unfortunately,relevant such notebooks, that had been prepared on the same dataset, and in light of thesame analysis task, are often nonexistent or unavailable. In this work, we describe ATENA-PRO, a framework for auto-generating such relevant, personalized exploratory sessions. Using a novel specification language, users first describe their desired output notebook. Our language contains dedicated constructs for contextually connecting future output queries. These specifications are then used as input for a Deep Reinforcement Learning (DRL) engine, which auto-generates the personalized notebook. Our DRL engine relies on an existing, general-purpose, DRL framework for data exploration. However, augmenting the generic framework with user specifications requires overcoming a difficult sparsity challenge, as only a small portion of the possible sessions may be compliant with the specifications. Inspired by solutions for constrained reinforcement learning, we devise a compound, flexible reward scheme as well as specification-aware neural network architecture. Our experimental evaluation shows that the combination of these components allows ATENA-PRO to consistently generate interesting, personalized exploration sessions for various analysis tasks and datasets.