Dewatering systems used for mining and quarrying operations often result in highly artificial and complex groundwater conditions, which can be difficult to characterise and monitor using borehole point sampling approaches. Here automated time-lapse electrical resistivity tomography (ALERT) is considered as a means of monitoring subsurface groundwater dynamics associated with changes in the dewatering regime in an operational sand and gravel quarry. We considered two scenarios: the first was unplanned interruption to dewatering due to a pump failure for a period of several days, which involved comparing ALERT monitoring results before and after groundwater rebound; the second involved a planned interruption to pumping over a period of 6 h, for which near-continuous ALERT monitoring of groundwater rebound and drawdown was undertaken. The results of the second test were analysed using distribution guided clustering (DGC) to provide a more quantitative and objective assessment of changes in the subsurface over time. ALERT successfully identified groundwater level changes during both monitoring scenarios. It provided a more useful indication of the rate of water level rise and maximum water levels than piezometer monitoring results. This was due to the piezometers rapidly responding to pressure changes at depth, whilst ALERT/DGC provided information of slower changes associated with the storage and delayed drainage of water within the sediment. By applying DGC we were able to automatically and quantitatively define changes in the resistivity sections, which correlated well with the direct observations of groundwater at site. For ERT monitoring applications that generate numerous time series, the use of DGC could significantly enhance the efficiency of data interpretation, and provide a means of automating groundwater monitoring through assigning alarm thresholds associated with rapid changes in groundwater conditions.