Health assessment (HA) & remaining useful life (RUL) estimation, the two essential pillars of the prognostics and health management (PHM) paradigm, help improve industrial equipment reliability while reducing maintenance costs. However, reported works treat HA and RUL estimation as disjoint problems though there exist unexploited similarities among these related issues. Additionally, in practical industrial working scenarios, equipment(s) stay in a normal condition for most of its lifespan, leading to a disproportionate training dataset, hampering the prediction accuracy. To overcome the above problems, we propose a data-driven multi-task learning framework aided by a novel least squares recurrent auxiliary classifier generative adversarial network (LS-R-ACGAN). LS-R-ACGAN employs recurrent neural networks (RNNs) in its generator & discriminator networks for multi-variate fault data generation while overcoming the vanishing gradient problem of ACGANs. Post-data-augmentation, a balanced training dataset, trains a multi-task learning model based on a deep gated RNN (DGRU) for joint HA and RUL estimation. Our simulations use the C-MAPSS dataset for testing the proposed approach’s accuracy. The final results showcase improvements by at least <inline-formula xmlns:mml="http://www.w3.org/1998/Math/MathML" xmlns:xlink="http://www.w3.org/1999/xlink"> <tex-math notation="LaTeX">$\sim$</tex-math> </inline-formula> 3.54% and <inline-formula xmlns:mml="http://www.w3.org/1998/Math/MathML" xmlns:xlink="http://www.w3.org/1999/xlink"> <tex-math notation="LaTeX">$\sim$</tex-math> </inline-formula> 2.38% on the RMSE and Score metric over existing state-of-the-art works suggesting its competitiveness and competence for real-world implementations. <italic xmlns:mml="http://www.w3.org/1998/Math/MathML" xmlns:xlink="http://www.w3.org/1999/xlink">Note to Practitioners</i> —This study attacks multiple presumptions concerning the maintenance of complex systems including, ample availability of fault samples alongside normal samples and solving only one of the problems, i.e., health assessment (HA) or remaining useful life (RUL) estimations rather than both. Popular artificial intelligence (AI) based solutions rely heavily upon the quantity of training data for desired performance outcomes. However, in real-life industrial scenarios, fault instances are rare, inherently resulting in an imbalanced dataset. Additionally, it is both labor-intensive and costly to repeat multiple experiments for gathering required data as the equipment(s) pass through short-lived fault states. Thus conventional AI-based solutions may end up producing biased predictions. This work proposes to solve the imbalanced training dataset problem along with joint HA and RUL estimations, in one solution pipeline, currently unexplored in majority of the existing works in the literature. LS-R-ACGAN generates ample diverse fault samples for reducing the degree of imbalance between normal and fault classes. Subsequently, after data augmentation, the balanced training dataset helps train a multi-task learning model for joint HA and RUL estimations. The proposed framework has been implemented and tested on a benchmark dataset proving its superiority over multiple existing methods in the literature.