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Isaiah 16:8

ESV For the fields of Heshbon languish, and the vine of Sibmah; the lords of the nations have struck down its branches, which reached to Jazer and strayed to the desert; its shoots spread abroad and passed over the sea.
NIV The fields of Heshbon wither, the vines of Sibmah also. The rulers of the nations have trampled down the choicest vines, which once reached Jazer and spread toward the desert. Their shoots spread out and went as far as the sea.
NASB For the fields of Heshbon have withered, the vines of Sibmah as well; The lords of the nations have trampled down its choice clusters Which reached as far as Jazer and wandered to the deserts; Its tendrils spread themselves out and passed over the sea.
CSB For Heshbon's terraced vineyards and the grapevines of Sibmah have withered. The rulers of the nations have trampled its choice vines that reached as far as Jazer and spread to the desert. Their shoots spread out and reached the sea.
NLT The farms of Heshbon are abandoned; the vineyards at Sibmah are deserted. The rulers of the nations have broken down Moab — that beautiful grapevine. Its tendrils spread north as far as the town of Jazer and trailed eastward into the wilderness. Its shoots reached so far west that they crossed over the Dead Sea.
KJV For the fields of Heshbon languish, and the vine of Sibmah: the lords of the heathen have broken down the principal plants thereof, they are come even unto Jazer, they wandered through the wilderness: her branches are stretched out, they are gone over the sea.

What does Isaiah 16:8 mean?

In this passage, Isaiah has commanded everyone to mourn the loss of the raisin cakes of Kir-hareseth (Isaiah 16:7). These cakes were apparently a well-loved delicacy that may have been exported to other nations. The production of the raisin cakes was lost when the invading armies destroyed the cities of Moab. Moab's economy and agricultural would have been decimated by the invasion, taking away the means that made the nation wealthy. This mourning, in a way, maintains a separation from the arrogant people of Moab, who are effectively told to grieve for themselves (Isaiah 16:6).

Isaiah goes into further detail regarding the destruction of the nation of Moab. He describes the deteriorating fields of Heshbon in the north. Nearby, the vine of Sibmah has also been struck down, perhaps by Assyria. Poetically, he says this grapevine thrived and reached Jazer, then farther north, and reaching all the way to eastern deserts. The vine's tendrils crossed over the Dead Sea into Israel. This symbolically depicts the successful distribution of the Moabite fields. Their crops spread prolifically around the region.

The grapes used to make the raisin cakes and other products are now gone. This ends both the enjoyment of the grapes and all the economic trading those products created to the north, east, and west. In other words, Moab's suffering had just begun with the attacks. Those who survived would not be able to return to the lives they once knew.
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