The ongoing selection for increased litter size has had significant impacts on sow husbandry practice. The present study investigated factors associated with farrowing duration and the proportion of sows that had prolonged farrowing in modern hyperprolific sows kept in a free farrowing system in a tropical environment. Farrowing data from 2493 Landrace x Yorkshire cross-bred sows in a commercial swine herd in Thailand were included in the study. The time of farrowing, parity number, litter size, and the birth status of each piglet were recorded. Farrowing duration was analysed using multiple analyses of variance. Total number of piglets born per litter (TB), parity, and time onset of farrowing were included in the statistical models. On average, TB, piglets born alive, and farrowing duration were 13.7, 12.1, and 221.0 min, respectively. Of these sows, 26.4% had TB ≥ 16 and 21.7% had a prolonged farrowing duration (≥300 min). Farrowing duration was positively correlated with TB (r = 0.141, p < 0.001), percentage of stillborn (SB) piglets per litter (r = 0.259, p < 0.001), percentage of mummified foetuses (MF) per litter (r = 0.049, p = 0.015), piglet birth weight (r = 0.068, p < 0.001), and litter birth weight (r = 0.041, p = 0.043). The proportion of SB per litter was higher and piglet birth weight lower in litters that had ≥16 TB than those with 8–12 TB (p < 0.05). The farrowing duration of sows with parity numbers 5–7 (247.7 ± 5.1 min) and 8–10 (237.1 ± 5.1 min) was longer than that of sows with parity numbers 1 (188.3 ± 5.2 min) and 2–4 (214.3 ± 3.9 min) (p < 0.05). Sows that had started farrowing during working hours had longer farrowing durations (229.3 ± 3.6 min) than those that had started farrowing during non-working hours (217.6 ± 3.4 min, p = 0.017). In multiparous sows, the duration of farrowing was positively correlated with the maximum temperature (r = 0.056, p = 0.012) and the maximum temperature–humidity index (r = 0.059, p = 0.008) in the 7 days before farrowing. The present data confirm that TB, sow parity, and time of onset of farrowing are significant risk factors for a prolonged farrowing.