Many previous studies have primarily focused on the use of deep learning for interferometric processing or separate recognition purposes rather than targeted measurements of detected wellpads. The present study centered around the integration of deep learning recognition and interferometric measurements for Tengiz oilfield wellpads. This study proposes the optimization, automation, and acceleration of targeted ground deformation wellpad monitoring. Mask Region-based Convolutional Neural Network (R-CNN)-based deep learning wellpad recognition and consequent Small Baseline Subset Synthetic Aperture Radar Interferometry (SBAS-InSAR) analyses were used for the assessment of ground deformation in the wellpads. The Mask R-CNN technique allowed us to detect 159 wells with a confidence level of more than 95%. The Mask R-CNN model achieved a precision value of 0.71 and a recall value of 0.91. SBAS-InSAR interferometric measurements identified 13 wells for Sentinel-1 (SNT1), 8 wells for COSMO-SkyMed (CSK), and 20 wells for TerraSAR-X (TSX) located within the −54–−40 mm/y class of vertical displacement (VD) velocity. Regression analyses for the annual deformation velocities and cumulative displacements (CD) of wells derived from SNT1, CSK, and TSX satellite missions showed a good agreement with R2 > 95. The predictions for cumulative displacements showed that the vertical subsidence processes will continue and reach −339 mm on 31 December 2023, with increasing spatial coverage and the potential to impact a higher number of wells. The hydrological analyses in the Tengiz oilfield clearly demonstrated that water flow has been moving towards the detected hotspot of subsidence and that its accumulation will increase with increasing subsidence. This detected subsidence hotspot was observed at a crossing with a seismic fault that might always be subject to reactivation. The role of this seismic fault should also be investigated as one of the ground deformation-controlling factors, even though this area is not considered seismically active. The primary practical and scientific values of these studies were identified for the operational risk assessment and maintenance needs of oilfield and gas field operators.