Background- Premature births are on a rise. Mechanical ventilation (MV) is required by very low birth weight (VLBW) neonates with respiratory failure. Optimal extubation remains challenging, as approximately 30% of ventilated preterm infants fail extubation. The incidence and risk factors for extubation failure (EF) may vary from country to country. Methods- This prospective observational study was conducted among VLBW neonates to find the EF rate and risk factors. Results- Of the 60 enrolled neonates with a mean gestational age of 30.94±1.55 weeks and mean birth weight of 1198±201 grams, 25 (41.7%) failed extubation. The risk factors associated with EF were shock (0.002), use of vasopressor (0.005), presence of complications (pneumothorax, ventilator-associated pneumonia) (0.032), anemia (0.017), culture-positive sepsis (0.042), duration of MV (0.006), post-extubation FiO2 requirement (<0.001) and post-extubation blood gas parameters- pH (<0.001), PaCO2 (0.001), HCO3 (0.001), SPO2/FiO2 ratio (p<0.001). On multivariate regression, Silverman Anderson (SAS) Score ≥ 5 (OR 5.23; 95% CI 2.3-12; <0.001) and anemia (hemoglobin less than 12 gram/dl) (OR1.71;95%CI 0.96-3.06; 0.028) were significant risk factors. Significantly more babies in the EF group expired (0.002). Also, neonates who failed extubation had an increased length of NICU stay as compared to those who succeeded 27±14 vs 20±12 days (p=0.048). Conclusion- Forty-one percent of VLBW neonates failed extubation. Post extubation SAS of ≥ 5, anemia (hemoglobin less than 12 grams) were independent risk factors for EF. Neonates with EF had poor outcomes with more deaths and prolong NICU stay.