On September 22, 1910, an aeronautical prize was offered to encourage aviators to fly across the Alps using an airplane, with the first successful pilot to do so awarded the trophy. This challenge inspired pilot Weymann to make several attempts, especially on the 22nd, after he had previously tried and failed on September 19. For this flight, Weymann was piloting a biplane built by the Farman workshops, a well-known manufacturer of early aircraft. However, mechanical problems plagued his efforts, as the plane had already been improperly adjusted during his first attempt, which ended in failure. On September 22, 1910, Weymann faced ongoing technical difficulties, particularly with the aileron control wires, which did not perform well and hindered the plane's ability to climb high enough to cross the Simplon Pass, which rises 2,100 meters above sea level. His first attempt in the morning was made under lighter wind conditions, but his second attempt yielded uncertain results, with the plane only reaching an altitude of 1,300 meters due to unpredictable air currents. The final attempt was made under much stronger winds, which again led to failure. Despite Weymann’s persistence and the high stakes of the aeronautical prize, the mechanical challenges of the era made such a flight extremely difficult. The Simplon Pass, known for its steep terrain and unpredictable weather, was a formidable obstacle for early aviators. Weymann’s repeated attempts highlight the risks and technical limitations of early aviation. The event underscored the progress being made in aviation, even as it revealed the many challenges that still needed to be overcome. While Weymann did not succeed in crossing the Alps on this day, his efforts contributed to the broader narrative of early flight, where every attempt, whether successful or not, played a role in advancing the field.