[2][3] He mentioned his travels to Crete, Prussia, Lithuania, Crimea, Turkey, the Holy Land, France, Lombardy (i.e. what is known today as Northern Italy) and Spain, as well as being shipwrecked in the Black Sea.

After the death of his father in 1399, Oswald returned to the County of Tyrol and began a quarrel with his older brother Michael about their inheritance.

In 1407 he and his brother agreed on how to split the inheritance: Oswald received a third of Castle Hauenstein and the accompanying estates in Seis am Schlern.

In 1408, in preparation for a pilgrimage to the Holy Land, Oswald paid for a memorial stone to be installed on the wall of the cathedral in Brixen.

Later that year he returned to Tyrol, where he joined the Elefantenbund, an alliance of noblemen against Friedrich IV, who had been banned by King Sigismund for aiding the flight of Antipope John XXIII from the Council of Constance.

Oswald could not reach an agreement with his enemies and did not show up in Tirol Castle on August 24, 1422, opting rather to ride to Hungary, where he met King Sigismund.

However, because the burghers and peasants of Tyrol and the bishop of Brixen supported Count Friedrich, most of the nobles, including both brothers of Oswald, surrendered on December 17, 1423.

After Wilhelm von Starkenberg's capitulation on November 26, 1426, Oswald was the last nobleman feuding with Count Friedrich, and was summoned to the Landtag in Bolzano.

In 1430 King Sigismund summoned the nobles of the Holy Roman Empire to a Reichstag in the city of Nuremberg and Oswald with his brother Michael immediately left Tyrol to meet the King, who instead of going directly to Nuremberg undertook a two-month detour to the South German cities of Überlingen and Constance to celebrate Christmas.

During this period, Oswald wrote many songs of an erotic nature, the most famous being "Ain Graserin" (KL 76) about a bathing maid, whose "frizzy hair" between her legs leads a man to have sex with her on the spot.

The unpleasantness of his visit inspired him to write the complaint-song "Wer die ougen vil verschüren", which he set to a French melody.

After over a year of negotiations, Sigismund was crowned Holy Roman Emperor on May 31, 1433, by Pope Eugenius IV, with Oswald probably in attendance.

Oswald became one of five military commanders and was tasked with the defense of the most important of all positions, the Mühlbacher Klause (Mühlbach fortress), which blocked the most likely invasion route from Styria, where King Friedrich had taken up residence.

On December 10, a Tyrolean delegation arrived in Graz to demand the release of Sigismund and the return of the county's treasures, taken by Friedrich in 1440.

The next session by the Landstände began in Merano on May 16, 1445, and as it was now clear that King Friedrich was not planning an attack, options were discussed on how to bring Sigismund to Tyrol.

An examination of his skull from a 1973 exhumation revealed that this was due to a congenital defect: his right eye socket was smaller than the left, which meant that his right eyeball was under constant pressure, resulting in ptosis, or a withering of the right eyelid muscles.

[5] Dieter Kühn's biography of Oswald, which attributes the "loss" of the right eye to an archery mishap when the boy was eight years old, is now generally discredited.

A popular theory that the eye was lost during the siege of Greifenstein Castle in 1423 is also implausible, as portraits of Oswald from 1408 already depict him with a drooping eyelid.