Simple Summary:In grazing systems, the use of novel technologies such as electronic feeders and automatic weighing systems enables collection of daily data of cattle feeding behaviour and growth. These technologies can be useful to study animal response to varying forage quantity and quality within and throughout grazing periods and seasons. The aim of this 254-day experiment was to investigate the effect of forage type, quantity, and quality on the consumption of a self-fed supplement (molasses-lick blocks (MLB)) and on the growth rate and feeding behaviour of grazing beef cattle. Results indicated that type and amount of forage affect MLB intake and feeding behaviour. Thus, when feed availability is low (e.g., forage on the paddock is depleted), animals increase consumption of and number and duration of visits to the supplementary feed. The use of MLB only improved growth rate of cattle when animals grazed sorghum and pasture or were fed oaten hay. Monitoring the feeding behaviour of animals around MLB reflects changes in forage quantity and quality.Abstract: Supplement intake and liveweight (LW) data were collected daily and remotely by digital in-paddock technologies (electronic feeder (EF) and walk-over-weighing scale (WOW)) to study the effect of forage quantity and quality on the intake of a self-fed supplement (molasses-lick blocks (MLB)), LW, liveweight change (LWC), and feeding behaviour of grazing beef cattle. Fifty-two crossbred weaners were rotationally grazed or fed for 254 days on different forages: sudangrass (SG), autumn pastures (P), winter pastures with concentrate (P+C), oat crops (OC), lucerne hay (LH), and oaten hay (OH). Forage quantity and quality were measured on the day of entry (high feed availability) and exit (low feed availability) stages of grazing or hay delivery. The intake of MLB was 111% higher (p < 0.05) at low compared to high feed availability, and this was also reflected in the feeding behaviour of animals (e.g., greater feeding frequency and rate). Moreover, there was a large temporal variability of daily MLB intake (Coefficient of variation (CV) = 146.41%). Supplementing MLB improved LWC only with SG, P, or OH (p < 0.05). The behaviour of animals around MLB reflects changes in feed quantity and quality and could be used to enhance cattle grazing and nutritional management in real time.