At the foot of the hill, there are heaps of pottery shards, indicating how large and active this settlement was. Among these shards were fragments of pottery with the king's seal, meaning they were used to pay taxes in the form of wine and oil to Jerusalem. Notably, an English archaeological expedition in the late 19th century found a clay tablet with cuneiform writing from the 8th century BCE at Tel Azekah. The site’s location and significance were the main reasons Azekah was the first target in Sennacherib’s campaign in 701 BCE, during which Assyria destroyed all the cities of Judah except Jerusalem. The Azekah Inscription, an Assyrian inscription preserved in the British Museum attributed to Sennacherib, describes the Assyrian conquest:

"The god Ashur bolstered my spirit, and I set out for the land of Judah. Along my journey, I received the tribute of the kings of the land of Philistia. With the aid of the god Ashur, my lord, I conquered the district of Hezekiah of Judah like [...] The city of Azekah, his fortified city, which is located between my border and the land of Judah, which like a nest of eagles sits on a mountain ridge like iron daggers, its towers reaching the sky. Its walls are fortified and rival (in height) the towering mountains. To the eye, it appears as if its peaks rise from the heavens. I besieged the city with packed ramps, with strong battering rams brought close, with the fierce assault of my infantry... They saw the attack of my horses, they heard the voice of the formidable armies of the god Ashur, and their hearts feared... I surrounded the city of Azekah and captured it, plundered its loot, destroyed it, ravaged it, and burned it with fire."

Azekah was rebuilt during the 7th century BCE, and by the early 6th century BCE, when Judah was attacked by the Babylonian army, it had again become one of the important border cities on the kingdom's western frontier. When the Babylonians besieged Jerusalem on the eve of the First Temple’s destruction, the prophet Jeremiah described the fate of the last two remaining cities in the Judean lowlands:

"The army of the king of Babylon fought against Jerusalem and all the cities of Judah that were left: against Lachish and Azekah, for these were the only fortified cities remaining in Judah."