The trouble began two years earlier. In April 1757, Spain established the San Saba Mission near present-day Menard, Texas, along with a military post, Presidio San Luis de las Amarillas, three miles away. The mission's purpose was to convert the Lipan Apache and extend Spanish influence onto the Great Plains while checking growing French influence among the northern tribes. The strategy backfired catastrophically. On March 16, 1758, a Wichita army described as 2,000 strong destroyed the San Saba Mission, killing two Franciscan priests and several converts. The nearby presidio, staffed by fewer than 100 soldiers, could only watch. Raids continued through 1759. Ortiz Parrilla, an experienced soldier, organized a punitive expedition: 636 men including 139 Spanish soldiers, 241 militiamen, 134 Apache, 30 Tlaxcalans, 90 Christian mission natives, and two priests, supported by two cannons and 1,600 horses, mules, and cattle.

The Taovaya, the most important of the Wichita tribes, had recently migrated south from Kansas and northern Oklahoma, pushed by Osage expansion. In the early 1750s, they established twin villages straddling the Red River -- one in what is now Jefferson County, Oklahoma, and one at present-day Spanish Fort, Texas. A French-brokered alliance with the Comanche in 1746 had made these villages a bustling trade center. Comanches brought Apache slaves, horses, and mules to exchange for French gunpowder, lead balls, knives, textiles, and Taovaya-grown corn, melons, squash, and tobacco. The villages were agricultural hubs and commercial crossroads, nothing like the vulnerable camps the Spanish expected to find.

On October 2, Ortiz Parrilla's column found and attacked a Yojuane village along the Clear Fork of the Brazos near present-day Graham, Texas, killing 49 and capturing 149. Captive Yojuanes offered to guide the Spanish north to the Taovaya stronghold. When the Spanish arrived at the Red River on October 7, they deployed with Tlaxcalans and mission forces on the right, Spanish soldiers in the center, and Apache on the left. The plan was to storm the fortress behind cannon fire. It failed utterly. Warriors sallied from the fort in repeated assaults. Each mounted warrior had two men on foot carrying extra loaded muskets. Eleven volleys of Spanish cannon fire could not breach the palisade. After four hours, the natives had captured both cannons. Nineteen Spanish soldiers were dead and fourteen wounded. Men had deserted. The priests and officers petitioned Ortiz Parrilla to withdraw.

The next morning, Ortiz Parrilla ordered the retreat to San Saba, arriving October 25 with his Yojuane captives, who were later sold into slavery -- the Yojuane soon vanished from history, their survivors absorbed by the Tonkawa. The Spanish estimated 100 native dead, almost certainly an exaggeration. Neither side followed up with serious military action. The Wichita tribes eventually sought peace with Spain and stopped raiding. In 1767, Spain abandoned the San Saba mission and its effort to Christianize the Apache. The battle's location -- whether on the Texas or Oklahoma side of the Red River -- remains uncertain. Archaeological traces of the fortified village on the Oklahoma side are now called the Longest site. The engagement marked the high-water mark of Spanish military ambition on the southern Great Plains, the place where European colonialism met organized, French-armed, fortress-building indigenous resistance and came away bloodied.