In road construction, it can happen that, for different reasons, the time between hot-mix asphalt (HMA) production and paving is extended to some hours. This can be reflected in several problems such as mix cooling and temperature segregation, but also in an extremely severe bitumen ageing due to its prolonged exposure to high temperatures. This paper deals with the investigation of these phenomena both in the laboratory and on site. In particular, the first part of the research aimed at observing the influence of the conditioning time, when the loose HMA is kept in the oven at a high temperature, on the mix properties. The second part focused on the ageing/cooling that happens on site during HMA hauling, as a function of time and type of truck. Temperatures were monitored using a thermal camera and different probes, and gyratory compactor specimens were produced by sampling some HMA from the trucks every 1 h for 3 h. The results showed that HMA stiffness rises if the time when the loose mix stays in the laboratory oven before compaction increases. However, on site, the HMA volumetric and mechanical properties do not change with hauling time up to 3 h, probably because the external material in the truck bed protects the HMA core from the access of oxygen, hindering bitumen oxidation and loss of volatiles. The temperature monitoring highlighted that temperature segregation, after 3 h hauling, can be higher than 30 °C but it can be reduced using insulated truck beds.