The rule of Peter Aron (r. 1451–1452; 1454–1457, with interruptions) marked the beginning of Moldavia's allegiance to the Ottoman Empire. It was during his reign that Moldavia agreed to pay tribute to Sultan Mehmed II “the Conqueror” (r. 1444–1446; 1451–1481), for the first time. Contemporary sources—chronicles, imperial charters, letters, petitions, reports, etc.—are not particularly straightforward on the nature of the initial interactions between Moldavia and the Ottomans. It appears that Moldavia was forced to recognize Ottoman suzerainty and pay an annual tribute to the Porte sometime soon after the fall of Constantinople in 1453. The exact date at which Moldavia became a tributary state (Ottoman-Turkish: kharâj-güzar; Latin: tributarius) is difficult to establish. But it is known that a peace agreement or treaty (‘ahdnâme) with the Porte was ratified sometime after 1455, during the second reign of Peter Aron. Sultan Mehmed II issued a document to Peter Aron on October 5 in which he outlined the conditions of a peace settlement between Moldavia and the Porte, requesting a punctual annual payment of two thousand Hungarian gold forints (ducats) in return for peace. The agreement reads:

On June 9, 1456, the Sultan sent another letter to the Moldavian prince in which he recognized Peter's acceptance of the peace conditions—an action that is said to have “eliminated the hostility” between these two leaders and their domains.

Moldavia declared its independence from Hungary around 1359, a few years after Dragoş, who was from Maramureş—a territory in northern Transylvania—settled in the region. Dragoş was sent by the Hungarian Crown to the east of the Carpathian Mountains to establish a local defensive zone against Tatar threats from the east. Dragoş “dismounted his horse,” as the Moldavian chronicles indicate, somewhere near Suceava, settled there with his family and men, and governed the northern parts of the territory of medieval Moldavia until about 1354 when his son, Sas, took control under the title of Markgraf or Marquis (r. ca. 1354–ca. 1363). During these years, Moldavia remained under Hungarian suzerainty. The situation changed before the sixth decade of the fourteenth century when the Drăgoşeşti broke their alliance with Hungary. A document from March 20, 1360, issued by Louis I “the Great” (King of Hungary from 1342 and King of Poland beginning in 1370 and until his death in 1382), reveals his gratitude toward a certain Dragoş from Giuleşti and his sons who restored Hungarian control over the territory of Moldavia. This need to “reclaim” Moldavia may have come from an internal uprising against the Hungarian Crown toward the end of 1359 or early 1360, likely led by Sas, his father Dragoş, and their followers.

Sometime between spring 1360 and winter 1364/1365, Bogdan I, also from Maramureş, crossed the Carpathians but this time to escape a conflict with the Hungarians. He overturned the control of the Drăgoşeşti and took the throne of the region as ruler (r. ca. 1363–1367). After Bogdan I took the throne, the territory to the east of the Carpathian Mountains was known both as Moldavia and Bogdania, that is, the realm of Bogdan. A document from February 2, 1365, speaks of the ruler Bogdan and his sons (“Bokdan voyvoda et sui filii”) crossing secretly into Moldavia and engaging in a tough battle against Sas, his sons, and their supporters. Bogdan emerged victorious from this encounter that took place sometime in 1363. Furthermore, his actions reveal that he also took advantage of the political and military situation and interests of his neighbours at this time. For example, Algirdas, ruler of the Grand Duchy of Lithuania from 1345 to 1377 had just secured the borders of his realm from Tatar attacks after the Battle of Blue Waters (1362–1363).

The beginnings of the principality of Moldavia in 1359 are somewhat shrouded in mystery, but several important leaders shaped the political, economic, and cultural position of the principality, including Peter I Muşat, Alexander I, and Stephen III. From the second half of the fourteenth century onward, Moldavia found itself at the crossroads of different cultures, among them Western and Central European, Byzantine, Slavic, and even Islamic. The networked position of this Carpathian principality enabled it to foster political, military, economic, and cultural ties with its closer and more distant neighbours. Contact and exchange facilitated the local assimilation of elements from various traditions that gave rise to distinct cultural and visual forms in Moldavia. This visual syncretism is most evident in the artistic and architectural spheres, both secular and ecclesiastical. The numerous fortifications of the principality and the dozens of fortified monasteries exhibit design and stylistic forms drawn from distinct traditions and adapted alongside local models. These structures were strategically erected along the perimeter of Moldavia in efforts to ensure the principality's protection from all sides. The secular and the religious spheres thus complemented each other and worked to further the protection of the land.

But it was especially from Stephen's rule in 1457—just a few years after the fall of Constantinople to the Ottomans in 1453—that Moldavia as a polity began to assume a crucial role in the continuation and transformation of Byzantine traditions and legacies while serving as a “shield” for the rest of Europe in the face of the rapidly advancing Tatar forces and expanding Ottoman Empire. After the death of Stephen III, Moldavia entered a period of turmoil. His immediate heirs, Bogdan III (r. 1504–1517) and Stephen IV (r. 1517–1527) were unable to maintain harmony and peace. They struggled against outside threats and internally against members of the high nobility who often rose against them. Outside threats from neighbours and the Ottomans were ongoing and intensified during the initial years of the sixteenth century. In 1505, for example, Radu the Great (r. 1495–1508) led his Wallachian troops into Moldavia to take over the principality but was defeated. The following year, in 1506, the Polish armies, under Sigismund I, attacked Moldavia and advanced as far as Botoşani but they were eventually forced to retreat.

Having established the chronological development of Moldavia and the diplomatic and military encounters that shaped the principality in the second half of the fifteenth century, I now wish to shift attention to how ideologies and patronage both shaped and reflected Stephen III's reign and the circumstances of the second half of the fifteenth century.

Within Stephen's long reign, the 1460s and 1470s presented a crucial moment of transformation and renewal for the Moldavian prince, who, in his self-fashioning, was redefining his role and aspirations as an Orthodox Christian leader and defender. Stephen's princely ideology, moulded in part by his own ambitions, was also shaped by Moldavia's often-troubled relations with its Christian neighbours and with the Ottoman Empire in the second half of the fifteenth century—in the wake of which he was aspiring to be a notable Christian leader and protector of the Christian faith. As early as 1466 Stephen began to take an interest in the patronage of the monastic communities on Mount Athos, and also initiated construction on his princely mausoleum at Putna Monastery. In 1472, he married Maria of Mangup on the feast day of the Holy Cross, September 14—a marriage that incited an array of cultural, artistic, and ideological transformations for Moldavia and its ruler. The following year, Stephen put an end to the payment of tribute toward the Ottoman Porte, began referring to himself as tsar, and waged war against Wallachia in an effort to expand Moldavia's territory and create a Christian buffer zone along the eastern and southern slopes of the Carpathian Mountains against the advancing Ottoman armies. A little over a decade later, the peace treaty with the Ottomans in 1486 marked the end of a phase in which Stephen fervently fought for the protection of his domain while redefining his princely aspirations. Once Moldavia entered a period of political and military stability in 1486–1487, Stephen directed his attention toward the building of churches throughout his domain, beginning with the churches at Bădeuţi (Milişăuţi) and Pătrăuţi dedicated to St. Procopius and the Holy Cross, respectively.

Stephen's secular and ecclesiastical patronage during his long and prosperous reign—spanning almost half a century— was a direct reflection of his princely ambitions. His initial projects—secular in character and taking the form of fortresses and royal courts—reveal his concerns during the first decades of his reign with the much-needed protection of his domain.