This paper introduces SudokuSens, a generative framework for automated generation of training data in machine-learning-based Internet-of-Things (IoT) applications, such that the generated synthetic data mimic experimental configurations not encountered during actual sensor data collection. The framework improves the robustness of resulting deep learning models, and is intended for IoT applications where data collection is expensive. The work is motivated by the fact that IoT time-series data entangle the signatures of observed objects with the confounding intrinsic properties of the surrounding environment and the dynamic environmental disturbances experienced. To incorporate sufficient diversity into the IoT training data, one therefore needs to consider a combinatorial explosion of training cases that are multiplicative in the number of objects considered and the possible environmental conditions in which such objects may be encountered. Our framework substantially reduces these multiplicative training needs. To decouple object signatures from environmental conditions, we employ a Conditional Variational Autoencoder (CVAE) that allows us to reduce data collection needs from multiplicative to (nearly) linear, while synthetically generating (data for) the missing conditions. To obtain robustness with respect to dynamic disturbances, a session-aware temporal contrastive learning approach is taken. Integrating the aforementioned two approaches, SudokuSens significantly improves the robustness of deep learning for IoT applications. We explore the degree to which SudokuSens benefits downstream inference tasks in different data sets and discuss conditions under which the approach is particularly effective.