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By the beginning of the fifteenth century the region of Appenzell was under the personal control of the abbot of St. Gall, with the Prince-Abbot of St. Gall appointing agents or baliffs to rule over the region. The communities of Appenzell however favored councils appointed by the Landsgemeinde, a system allowing each citizen to vote. The success of the Swiss Confederation, which used similar systems, and which had defeated the powerful Habsburgs, encouraged the citizens of Appenzell to consider rebelling against St. Gall's control. During the late fourteenth century conflict between the abbot and Appenzell over grazing rights, taxes, and tithes had caused large disruptions. In 1376 a new Swabian League of Cities was founded, after being defeated by Count Eberhard II of Württemberg four years earlier, suffering the murder of the captain of the league, and the breach of the league's obligations by Emperor Charles IV. Under the leadership of Ulm, the cities of Biberach an der Riß, Buchhorn, Isny im Allgäu, Konstanz, Leutkirch im Allgäu, Lindau (Bodensee), Memmingen, Ravensburg, Reutlingen, Rottweil, St. Gallen, Überlingen, and Wangen im Allgäu, formed an alliance lasting the next four years. Additionally the city of Dinkelsbühl, an imperial city on the edge of Franconia, to the north-east of the Swabian region, joined the league, followed by cities from the Franconian heartland such as Rothenburg ob der Tauber and Windsheim.
The emperor Charles IV refused to recognize this league, and declared it a rebellion. Ulrich of Württemberg, son of Eberhard II, marched against the league in 1377, but was defeated at Reutlingen by an allied army. Later that year the emperor lifted his ban over the alliance, and established an arbitration court, which was rapidly extended over the Rhineland, Bavaria, and Franconia in response. That same year Appenzell joined the League, supported by St. Gallen, a city often at odds with the Abbey of St. Gall as well, and the city of Konstanz. Confident in its allies, Appenzell refused to pay a number of gifts and tithes to the Abbot Kuno von Stoffeln, and the loss revenue caused him to approached the Habsburgs for assistance. The Habsburgs came into an agreement with the abbot in 1392, and again in 1402. In response to this growing threat, Appenzell entered a formal alliance with the city of St. Gallen.
Conflict broke out between the inhabitants of Appenzell and agents of the abbot, including after one baliff's demands that a body be dug up because he wanted the man's clothes. An uprising broke out, and the agents of the abbot were driven out of Appenzell lands. Both Appenzell and the city of St. Gallen prepared for war, which in the city's case marked one of the first breaks between an abbot and his estates. In 1402 the Swabian League of Cities expelled Appenzell, perhaps fearful of retaliation from the Habsburgs. Later that same year the abbot of St. Gall and the city of St. Gallen reached an agreement, meaning the rebellious Appenzell could no longer count on the city's support. Instead they formed an alliance with the Canton of Schwyz the following year, while also receiving some support from Glarus, who authorized volunteers to aid Appenzell. The Swabian League of Cities joined the Habsburgs against Appenzell, and marched to St. Gallen, and then into Appenzell lands.
The allied army marched into the pass to Speicher, where they encountered Appenzell forces outside the village of Vögelinsegg. Initially only eighty Appenzellers stood against the league, marching from the defenders' position upon a nearby hill. 300 soldiers from Schwyz and 200 from Glarus moved alongside this small force to protect the flanks. The League ordered a charge against the forces of Appenzell, while at the same time marching a large cavalry force to flank both sides, in an effort of cutting off the Swiss from their defensive hill. About 5,000 Swabian soldiers charged against the Appenzeller line, while 1,000 cavalry attacked the combined 500 Swiss defenders. The Swabian infantry then surrounded the Swiss, who were largely unable to retreat up the hill. The cavalry in the front also helped to rally the Swabian forces, and collect them before a charge could be attempted up the hill. The main Appenzeller army, about 2,000 strong, charged from its high ground upon the hill, hoping to save the small army that was below. The Swabians braced themselves defensively, and repulsed the Appenzellers, taking only minimal casualties.
The decisive defeat of Appenzell's forces resulted in a peace treaty, signifying the abbot's possession of Appenzell. The peace did not last however, as Appenzell continued to demand its independence, growing closer to the city of St. Gallen.