What does Isaiah 27:2 mean?
ESV: In that day, "A pleasant vineyard, sing of it!
NIV: In that day— "Sing about a fruitful vineyard:
NASB: On that day, 'A vineyard of beauty, sing of it!
CSB: On that day sing about a desirable vineyard:
NLT: 'In that day, sing about the fruitful vineyard.
KJV: In that day sing ye unto her, A vineyard of red wine.
NKJV: In that day sing to her, “A vineyard of red wine!
Verse Commentary:
Isaiah begins another section describing what will happen during the end times. This time is often summarized as "that day" or "the day of the Lord" (Isaiah 2:11; Ezekiel 30:3; Obadiah 1:15; Acts 2:20; 2 Peter 3:10). When the Lord reigns on earth, a restored Israel will be like a pleasant or fruitful vineyard. Some manuscripts describe it as a "vineyard of wine."

Isaiah 5:1–7 also presented a vineyard song. There, the Lord destroyed His vineyard Israel because of injustice and unrighteousness. After carefully building and cultivating it, the Lord removed the protective hedge and wall around the vineyard. This allowed wild animals to come and destroy it. He also sent a drought over the vineyard and allowed thorns and briers to grow and take over.

When the Lord comes and destroys the wicked and makes Himself king of the entire world, the vineyard of Israel will be fully restored. The Lord Himself sings of it in the following verses.
Verse Context:
Isaiah 27:2–6 describes the restoration and redemption of Israel in the end times by the Lord. Isaiah pictures Israel in song as a pleasant vineyard tended and fully provided for. Her fruit will fill the world. God prefers that those within this vineyard who still oppose Him would repent, rather than being destroyed.
Chapter Summary:
This passage often uses the phrase "in that day" referring to the end times when the Lord reigns on earth as king. Then, the Israelites will be fully restored. Their "fruit" will fill the world. The nations God used as tools to judge His people will themselves be judged, but much more harshly. Defeats will happen in the meantime, but the Lord will only measure out enough discipline to trigger Israel's repentance. There will be no compassion for those who refuse to repent. He will bring all His people home to worship Him in Jerusalem in the end.
Chapter Context:
Isaiah 27 completes a section (Isaiah 24—27) about the time when the Lord will make all things right. That description begins with the Lord's judgment of the earth (Isaiah 24:1) and ends with the redemption and restoration of Israel (Isaiah 27:6). The nations God used to judge Israel will themselves be judged. The next section of Isaiah focuses on God's scathing words for those who opposed Him, including the failed leaders of Israel and Judah.
Book Summary:
Isaiah is among the most important prophetic books in the entire Bible. The first segment details God's impending judgment against ancient peoples for sin and idolatry (Isaiah 1—35). The second part of Isaiah briefly explains a failed assault on Jerusalem during the rule of Hezekiah (Isaiah 36—39). The final chapters predict Israel's rescue from Babylonian captivity (Isaiah 40—48), the promised Messiah (Isaiah 49—57), and the final glory of Jerusalem and God's people (Isaiah 58—66).
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