For the next century, the order organized annual colonialist reise (raids) into Samogitian and Lithuanian lands, without great success but at immense human cost.

Border regions in Samogitia and Suvalkija became sparsely inhabited wilderness due to ethnic cleansing, although the order gained very little territory.

Lithuania and its new ally, Poland, defeated the order in the decisive Battle of Grunwald in 1410, which is often cited as the end of the Lithuanian Crusade and the Polish–Lithuanian–Teutonic War.

[4]: 415  With the arrival of the first Teutonic crusaders, led by Hermann Balk, in Chełmno Land in 1230, the religious traditions of modern-day Estonia and Latvia began to slowly turn towards Catholicism.

Even with support from the Teutonic Order, the Christian Livonians suffered major defeats in the battles of Durbe (1260),[11] Karuse (1270), and Aizkraukle (1279).

These included the 1264 siege of Vėluva (Wehlau) castle in Sambia during the reign of Treniota and the revenge taken against Poland for the Yotvingians, led by Vaišvilkas and Švarnas.

[13] The Teutonic Order's principal objective was to conquer the Lithuanian lowland region, Samogitia, and build fortresses there to solidify their control.

[14] Starting with the reign of Gediminas, Lithuania also began rapidly expanding eastward, conquering Ruthenian lands and gaining more resources for its long-lasting wars.

When the battles around Jerusalem ceased after the Siege of Acre in 1291, Christian religious groups turned their military efforts toward eastern Europe and the Iberian Peninsula, intent on conquest or reconquest.

[5]: 13–14  The prospect of loot from the Grand Duchy of Lithuania and the State of the Teutonic Order exacerbated the conflict, and the conquests of both sides were often short-lived or haphazard.

[20] Teutonic soldiers commanded by Prussian Landmeister Konrad von Thierberg crossed the frozen Neman River and attacked the Lithuanian fortress in the morning.

[5]: 29  After initial successes by the crusaders, the two sides fought in the Battle of Turaida after Vytenis forged an alliance with the citizens of Riga, a city ostensibly under the control of the Livonian Order.

[25] To better demarcate and defend its eastern border against the Lithuanian advances, the Teutonic Order took to erecting small fortresses and fortified houses.

[18]: 53–54  But the Christian population's general fear of the "savage pagans" did not change with the victory, especially not among German colonists in rural areas of the order's territory.

[5]: 36  In 1336, a large army supported by John of Bohemia and his son-in-law, Henry XIV, crossed the Neman in Samogitia and attacked the castle of Pilėnai.

In 1349, Teutonic commander Winrich von Kniprode seized a victory against the Lithuanians in the Battle of Strėva, which was held in an open field.

[9]: 183  The poet and herald Peter Suchenwirt wrote a poem to commemorate the capture, when Kęstutis apparently swore an oath to convert to Christianity.

)[29]: 55  In response, Kęstutis and Algirdas gathered military contingents from all of Lithuania, from Russian feudal lords faithful to the grand duchy, and from the Tatars who were disposed to help because they shared a border with the Teutonic State near Königsberg.

Alternating alliances were forged with former opponents to the north and west since the question of Christian conversion had lost energy in the preceding century.

[39] The Lithuanian nobility were skeptical about assimilating into Polish culture, so Jagiełło had to concede more rights to Vytautas, who wanted to expand east into the Grand Duchy of Moscow and needed more freedom for military action.

[9]: 56–57 The leaders of the Teutonic Order were skeptical and uncertain about their future in the region after Jogaila accepted the Polish crown and Christianity while maintaining close ties to Lithuania.

[42] In order-controlled territories, Lithuanian discontent grew due to the ecclesiastical tithes and the restrictive regime imposed by the merchants of the Teutonic State.

With open support for rebellion in Teutonic Order territory, Grand Master Ulrich von Jungingen called for war.

[5]: 101 [47] In 1413, the new Teutonic grand master, Heinrich von Plauen, opposed the arbitration of an imperial envoy, Benedikt Makrai, who had assigned the Neman's east riverbank to the Lithuanians.

[5]: 226  Both the Lithuanian light cavalry and the armies of the order preferred to raid unprotected settlements before engaging in large-scale battles.

[4]: 425 In Germany, the conflicts were largely forgotten or limited to the dispute between the Teutonic Order and the Kingdom of Poland that ended with the Peace of Thorn.

[54]: 76  In history books printed from the 1800s on, the Lithuanian crusade was minimized or recounted in single favorable episodes, such as the Battle of Rudau or the construction of settlements by German colonists.

The historiographic record also includes the personal letters of the Lithuanian rulers Gediminas, Algirdas, and Vytautas, which were often written in Old Church Slavonic, German, or Greek.

[55]: 301  The 1986 theory of Gudavičius's student Alvydas Nikžentaitis, that Gediminas was poisoned, challenged the accepted Soviet view of Lithuanian history.

[55]: 289  The 1993 research of S. C. Rowell in Lithuania Ascending made it easy for other historians to examine the political and cultural context of the Lithuanian crusades.