Outdoor icephobic coatings are prone to damage, particularly in extreme weather conditions like freezing temperatures and acid rain. Damage to the coating will result in a loss of icephobic function and may lead to increased icing. Furthermore, it is imperative to incorporate sustainability into icephobic coatings as environmental consciousness grows. Herein, a vanillin-based icephobic coating with anti-extreme-environment self-healing was prepared by incorporating vanillin-based polyols into prepolymers terminated with isocyanates that include silicone oil. The coating exhibited low ice adhesion with a measurement of 8.8 kPa, which was mainly attributed to the hydrophobicity of PDMS and the hydrophobic and lubricating characteristics of silicone oil. Moreover, the coating's remarkable chemical stability and ability to resist fouling were due to its lubricating and hydrophobic properties. More importantly, the coating retains impressive self-healing abilities in extreme conditions (−20 °C, pH = 1, pH = 14) due to the multiple dynamic bonds within the coating and the water-repelling and plasticizing effects of silicone oil. The coating maintained its original hydrophobic characteristics and low ice adhesion strength even after several recycling and self-healing cycles, demonstrating remarkable lifespan and sustainability. This work facilitates meeting the need for anti-icing in outdoor areas, particularly in extremely cold, acidic, and alkaline conditions.