Thirty Years' War Historical population Year The city was successfully defended against Prince Maurice in 1601 and again in 1603, but the city eventually fell in the 1629 siege led by Frederick Henry. It was besieged several times by Prince Maurice of Orange, stadtholder of most of the Dutch Republic, who wanted to bring 's-Hertogenbosch under the rule of the rebel United Provinces. During the Eighty Years' War, the city took the side of the Habsburg ( Catholic) authorities and thwarted a Calvinist coup.

The wars of the Reformation changed the course of the city's history.

Others held positions there: Matthaeus Pipelare was musical director at the Confraternity of Our Lady and renowned Habsburg copyist and composer Pierre Alamire did much of his work at 's-Hertogenbosch. The city was also a center of music, and composers, such as Jheronimus Clibano, received their training at its churches. Until 1520, the city flourished, becoming the second largest population centre in the territory of the present Netherlands, after Utrecht. The town suffered a catastrophic fire in 1463, which the then (approximately) 13-year-old Bosch probably witnessed presumably, this fire provided inspiration for the fiery hell-scapes that would later make Bosch famous. 's-Hertogenbosch became the birthplace and home of one of the greatest painters of the northern Renaissance period, Hieronymus Bosch. Artificial waterways were dug to serve as a city moat, through which the rivers Dommel and Aa were diverted.

In the late 14th century, a much larger wall was erected to protect the greatly expanded settled area.

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