As I sketched out in this answer, Ahaz's refusal to ask for a sign is critical to interpreting what follows. For what follows is not best conceived in context as a sign "designed to signify to Ahaz that the land will be delivered from its calamities." Rather, it is indeed a prophecy of judgment.

Ahaz was already told that the Syrian/Ephraim alliance would fail (Isa 7:7-9). When the LORD has Isaiah ask Ahaz to indicate a sign (v.10-11), Ahaz's refusal to (v.12) is not looked upon with favor. Verse 13 is then a key shift in the narrative to the prophecy (NKJV):

Then he said, “Hear now, O house of David! Is it a small thing for you to weary men, but will you weary my God also?

Two things are critical to see:

  1. Ahaz's refusal to do what the LORD asked of him is wearying to God, as much of the behavior of the lineage of David had been (both the "you" references in the verse are plural, not singular, in the Hebrew). So Ahaz is being addressed, but obliquely in his connection to the lineage of David, which leads to the second point...
  2. Ahaz is no longer the sole referent, but rather the referent expands to the "house of David" (any and all those in the line of David, Ahaz included, but not exclusively or even necessarily to him alone). So the prophecy is for the "house of David" to pay attention to, such that when it is fulfilled, they will take notice of it.

The following prophecy is twofold:

  1. A child will be born under specific circumstances (see the previous answer linked to with respect to the virgin aspects, but also below for a key footnote I had there that is really more related to this question [hence why it was a footnote in the other question]), a child whose name implies God is with His people again (Isa 7:14-16)
  2. But more immediately, judgment to Judah will be coming (i.e., God not with His people). That judgment is not by the Syria/Ephraim alliance (that was already made clear), but rather by Assyria (Isa 7:17-25), the nation Ahaz would look to for help against the alliance (2 Kings 16), which judgment comes about in Ahaz's son Hezekiah's days (2 Kings 18), though Jerusalem is spared (and Judah for a time) because of Hezekiah's looking/prayer to God (2 Kings 19:20).

As to how the prophecy of Isa 7:14-16 can be conceived as fulfilled in Christ, I'll reproduce from what was my text in footnote 1 in the other answer I linked to above, but fits better in the text of this answer. Everything between the horizontal breaks was originally part of n.1 in that answer.


Note that the only immediate point of v.15-16 is that one land abhorred by Ahaz that has two kings over it will cease to have kings by the time this child of Isa 7:14 is very old. Almost unanimously commentators will identify these two kings with Rezin and Pekah (Remaliah's son), identifying the single land as symbolically illustrating the united forces of two lands (quotes from commentaries found at the preceding link):

The "land" must certainly be that of the two confederate kings, Rezin and Pekah, the Syro-Ephraim-itic land, or Syria and Samaria (Pulpit Commentary)

The countries of Syria and Israel, which Ahaz abhorred for their cruel designs and practices against him (Benson Commentary)

Syria and Samaria regarded as one (2Ki 16:9; 15:30) (Jamieson-Fausset-Brown Bible Commentary)

Ephraim and Syria are treated as one territory, ruled by the two allied kings (Cambridge Bible for Schools and Colleges)

But this is God's message, and though the sign is broadly to the house of David, the last part of v.16 relates it to Ahaz with "The land that thou abhorrest shall be forsaken of both her kings" (KJV). Most later translations have "dread" in place of the idea of abhor, as the word can have either idea (see BDB), and Ahaz's fear is known from v.4.

However, if one understands it as abhor (repugnance) rather than dread (fear), it can be argued that the reference God is making is to the literal singular land of the divided monarchy, that is, Israel and Judah. Ahaz has demonstrated to God his abhorrence for the land in his great wickedness (2 Kg 16:2-4; 2 Ch 28:1-4)—note the various immoral uses of the land in the references, and of course the actions themselves would lead to judgment upon the land. Ahaz's true abhorrence was for the land God had given.

Viewed so, the prophecy fits Christ exactly, for what it is saying is that Israel and Judah (the one divided land, that land abhorred by Ahaz) will both have ceased to have their kings during the early years of the child prophesied in Isa 7:14.

This is not true of Ahaz's day (Judah remained with a king). It is also not true of the time of the Babylonian captivity (no such child was born during that time). But it is true of Christ. A king (Jewish, but not Davidic) was reestablished during the time of the Maccabees in the Hasmonean dynasty:

From 110 BC, with the Seleucid empire disintegrating, the dynasty became fully independent, expanded into the neighbouring regions of Galilee, Iturea, Perea, Idumea and Samaria, and took the title "basileus" [king].

This dynasty was replaced by the Herodian dynasty, with the new king, Herod the Great:

The installation of Herod the Great (an Idumean) as king in 37 BC made Israel a Roman client state and marked the end of the Hasmonean dynasty.

He "was appointed 'King of the Jews' by the Roman Senate," but the more significant point is that:

When Herod died in 4 BCE, the kingdom was divided among his four sons into tetrarchies, the largest being the Tetrarchy of Judea.

The land of Israel was once again without a king, but this time during the youth of the one named Immanuel, Jesus Christ!

Scholars generally accept a date of [Christ's] birth between 6 and 4 BC. It is generally agreed that Herod the Great died in 4 BCE, placing the birth of Jesus before then.

Then v.17ff goes on to describe the process by which Israel and Judah will begin to lose power (and lose their kings), beginning with Israel (and even Judah is greatly affected by Assyria, so Isaiah 8:8).


Conclusion

Ahaz refused a sign, so he was not specifically given one, but the house of David more broadly was given a sign that God would be with them, the birth of a child named Immanuel under specific circumstances. That sign only and uniquely came to pass at the birth of Jesus Christ, per the statement of Matthew 1:22-23.

Answer from ScottS on Stack Exchange
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Isaiah 7:14 Therefore the Lord Himself will give you a sign: Behold, the virgin will be with child and will give birth to a son, and will call Him Immanuel.
Therefore the Lord Himself will give you a sign: Behold, the virgin will be with child and will give birth to a son, and will call Him Immanuel.
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Jean E. Jones
jeanejones.net › home › “the virgin shall conceive”: why isaiah 7:14 confuses people
"The Virgin Shall Conceive": Why Isaiah 7:14 Confuses People - Jean E. Jones
December 22, 2021 - Apologetics, Bible Perplexities, Jesus in the Old Testament, Old Testament · For many years, the prophecy that confused me most was Isaiah 7:14: “Behold, the virgin shall conceive and bear a son, and shall call his name Immanuel.” Every Christmas I heard pastors quote this, but none had ...
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How can the virgin birth in Matthew 1:22 be a fulfilment of Isaiah 7:14? - Biblical Hermeneutics Stack Exchange

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December 27, 2016
Therefore the Lord himself shall give you a sign; Behold, a virgin shall conceive, and bear a son, and shall call his name Immanuel. Butter and honey shall he eat, that he may know to refuse the evil, and choose the good. For before the child shall know to refuse the evil, and choose the good, ... More on hermeneutics.stackexchange.com

Why is Isiah 7:14 translated "virgin will conceive"?

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10
June 10, 2020

A Greek translation of Hebrew almah is parthenos, which can mean both "young woman" as well as "virgin."

There's a bit more detail in this thread.

More on reddit.com

Isaiah 7:14 is not necessarily a prophecy about Jesus.

🌐 r/DebateReligion
91
July 29, 2020
That's absolutely correct: Isaiah 7 is not about Jesus. It's a prophecy that was given to Ahaz. It even goes on to say "before the boy knows enough to reject the wrong and choose the right, the land of the two kings you dread will be laid waste". So it pretty clearly isn't about Jesus, since it was fulfilled quite quickly. So what's going on in Matthew then? Notice that not even Matthew calls it a prophecy. Usually by "prophecy" we think of "an event predicted before it happens and then it happens". But Matthew does say it's "fulfilled". So Matthew sees the birth of Jesus as "fulfilling" the passage. This is a very interesting word, because it's also the word that Matthew uses for Jesus coming out of Egypt, by saying that Jesus fulfilled Hosea 11:1. This is crucial. Hosea 11:1 most certainly isn't a prophecy, as it's about a past event: the exodus of the Hebrews out of Egypt. So it's a sentence that talks about a past event, and yet Matthew still says that Jesus fulfils it hundreds of years later. I think what's happening here is something more like Matthew saying "The story of the scriptures find their ultimate completion in Jesus". Ahaz had a child born that would signify that they would be saved from their enemies. So too Jesus being born would bring salvation. Matthew also quotes Jesus as saying that He came to fulfil the Law of Moses, which should probably inform how we read these passages both ways. It's also worth nothing that while παρθένος is explicitly a virgin, almah would have most probably denoted a virgin. It doesn't mean virgin by definition, but culturally, it would have. Perhaps kind of like how "homeless" doesn't mean you don't own an investment property that you're currently renting out, but it strongly implies it. More on reddit.com

To Christians: Virgin is incorrectly translated in Isaiah 7:14, is should read Maiden or young women. Why do you still believe in the virgin birth?

🌐 r/DebateReligion
162
September 29, 2013
Firstly, it is worth remarking that Christian belief in the virgin birth is based off the accounts in Matthew and Luke, not from Isaiah. Secondly, I think most Christians on this sub are aware of this, and that "maiden" and "young woman" carry heavy connotations of virginity in a culture that tabooed premarital sex. A young, unmarried woman (as the term implies and is always used for) implies virginity in a Hebraic context. More on reddit.com
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Bibleref
bibleref.com › Isaiah › 7 › Isaiah-7-14.html
What does Isaiah 7:14 mean? | BibleRef.com
NIV Therefore the Lord himself will give you a sign: The virgin will conceive and give birth to a son, and will call him Immanuel. NASB Therefore the Lord Himself will give you a sign: Behold, the virgin will conceive and give birth to a son, and she will name Him Immanuel.
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Biblia
biblia.com › bible › esv › Is7.14,Mt1.23
Isaiah 7:14 ESV - Therefore the Lord himself… | Biblia
14 Therefore, the Lord Himself will give you a sign: The virgin will conceive, have a son, and name him Immanuel. 14 Therefore the Lord himself will give you a sign. Look, the young woman is with child and shall bear a son, and shall name him Immanuel.
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catholic.com › audio › ddp › a-virgin-shall-conceive
A Virgin Shall Conceive | Catholic Answers Podcasts
September 11, 2023 - DAY 254 CHALLENGE “Isaiah’s prophecy of Immanuel (Isa. 7:14) doesn’t apply to Jesus. It doesn’t say ‘a virgin shall conceive.’ The Hebrew word ‘al...
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How can the virgin birth in Matthew 1:22 be a fulfilment of Isaiah 7:14? - Biblical Hermeneutics Stack Exchange

As I sketched out in this answer, Ahaz's refusal to ask for a sign is critical to interpreting what follows. For what follows is not best conceived in context as a sign "designed to signify to Ahaz that the land will be delivered from its calamities." Rather, it is indeed a prophecy of judgment.

Ahaz was already told that the Syrian/Ephraim alliance would fail (Isa 7:7-9). When the LORD has Isaiah ask Ahaz to indicate a sign (v.10-11), Ahaz's refusal to (v.12) is not looked upon with favor. Verse 13 is then a key shift in the narrative to the prophecy (NKJV):

Then he said, “Hear now, O house of David! Is it a small thing for you to weary men, but will you weary my God also?

Two things are critical to see:

  1. Ahaz's refusal to do what the LORD asked of him is wearying to God, as much of the behavior of the lineage of David had been (both the "you" references in the verse are plural, not singular, in the Hebrew). So Ahaz is being addressed, but obliquely in his connection to the lineage of David, which leads to the second point...
  2. Ahaz is no longer the sole referent, but rather the referent expands to the "house of David" (any and all those in the line of David, Ahaz included, but not exclusively or even necessarily to him alone). So the prophecy is for the "house of David" to pay attention to, such that when it is fulfilled, they will take notice of it.

The following prophecy is twofold:

  1. A child will be born under specific circumstances (see the previous answer linked to with respect to the virgin aspects, but also below for a key footnote I had there that is really more related to this question [hence why it was a footnote in the other question]), a child whose name implies God is with His people again (Isa 7:14-16)
  2. But more immediately, judgment to Judah will be coming (i.e., God not with His people). That judgment is not by the Syria/Ephraim alliance (that was already made clear), but rather by Assyria (Isa 7:17-25), the nation Ahaz would look to for help against the alliance (2 Kings 16), which judgment comes about in Ahaz's son Hezekiah's days (2 Kings 18), though Jerusalem is spared (and Judah for a time) because of Hezekiah's looking/prayer to God (2 Kings 19:20).

As to how the prophecy of Isa 7:14-16 can be conceived as fulfilled in Christ, I'll reproduce from what was my text in footnote 1 in the other answer I linked to above, but fits better in the text of this answer. Everything between the horizontal breaks was originally part of n.1 in that answer.


Note that the only immediate point of v.15-16 is that one land abhorred by Ahaz that has two kings over it will cease to have kings by the time this child of Isa 7:14 is very old. Almost unanimously commentators will identify these two kings with Rezin and Pekah (Remaliah's son), identifying the single land as symbolically illustrating the united forces of two lands (quotes from commentaries found at the preceding link):

The "land" must certainly be that of the two confederate kings, Rezin and Pekah, the Syro-Ephraim-itic land, or Syria and Samaria (Pulpit Commentary)

The countries of Syria and Israel, which Ahaz abhorred for their cruel designs and practices against him (Benson Commentary)

Syria and Samaria regarded as one (2Ki 16:9; 15:30) (Jamieson-Fausset-Brown Bible Commentary)

Ephraim and Syria are treated as one territory, ruled by the two allied kings (Cambridge Bible for Schools and Colleges)

But this is God's message, and though the sign is broadly to the house of David, the last part of v.16 relates it to Ahaz with "The land that thou abhorrest shall be forsaken of both her kings" (KJV). Most later translations have "dread" in place of the idea of abhor, as the word can have either idea (see BDB), and Ahaz's fear is known from v.4.

However, if one understands it as abhor (repugnance) rather than dread (fear), it can be argued that the reference God is making is to the literal singular land of the divided monarchy, that is, Israel and Judah. Ahaz has demonstrated to God his abhorrence for the land in his great wickedness (2 Kg 16:2-4; 2 Ch 28:1-4)—note the various immoral uses of the land in the references, and of course the actions themselves would lead to judgment upon the land. Ahaz's true abhorrence was for the land God had given.

Viewed so, the prophecy fits Christ exactly, for what it is saying is that Israel and Judah (the one divided land, that land abhorred by Ahaz) will both have ceased to have their kings during the early years of the child prophesied in Isa 7:14.

This is not true of Ahaz's day (Judah remained with a king). It is also not true of the time of the Babylonian captivity (no such child was born during that time). But it is true of Christ. A king (Jewish, but not Davidic) was reestablished during the time of the Maccabees in the Hasmonean dynasty:

From 110 BC, with the Seleucid empire disintegrating, the dynasty became fully independent, expanded into the neighbouring regions of Galilee, Iturea, Perea, Idumea and Samaria, and took the title "basileus" [king].

This dynasty was replaced by the Herodian dynasty, with the new king, Herod the Great:

The installation of Herod the Great (an Idumean) as king in 37 BC made Israel a Roman client state and marked the end of the Hasmonean dynasty.

He "was appointed 'King of the Jews' by the Roman Senate," but the more significant point is that:

When Herod died in 4 BCE, the kingdom was divided among his four sons into tetrarchies, the largest being the Tetrarchy of Judea.

The land of Israel was once again without a king, but this time during the youth of the one named Immanuel, Jesus Christ!

Scholars generally accept a date of [Christ's] birth between 6 and 4 BC. It is generally agreed that Herod the Great died in 4 BCE, placing the birth of Jesus before then.

Then v.17ff goes on to describe the process by which Israel and Judah will begin to lose power (and lose their kings), beginning with Israel (and even Judah is greatly affected by Assyria, so Isaiah 8:8).


Conclusion

Ahaz refused a sign, so he was not specifically given one, but the house of David more broadly was given a sign that God would be with them, the birth of a child named Immanuel under specific circumstances. That sign only and uniquely came to pass at the birth of Jesus Christ, per the statement of Matthew 1:22-23.

Answer from ScottS on hermeneutics.stackexchange.com
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Isaiah 7:14 ESV: Therefore the Lord himself will give you a sign. Behold, the virgin shall conceive and bear a son, and shall call his name Immanuel.
“This Book [is] the most valuable thing that this world affords. Here is Wisdom; this is the royal Law; these are the lively Oracles of God.” With these words the Moderator of the Church of Scotland hands a Bible to the new monarch in Britain’s coronation service.
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“A virgin shall conceive and bear a son”: Keeping faith this Christmas - ABC Religion & Ethics
December 23, 2019 - “Behold, a virgin shall conceive and bear a son, and shall name him Immanuel” (Isaiah 7:14) — that is, “God with us.” When Saint Jerome in the fifth century designated the prophet Isaiah as an evangelist and the book of Isaiah as “the fifth gospel,” this passage must have been ...
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Isaiah 7:14 - Therefore the Lord himself will give you a sign: T...
The virgin will conceive a child! She will give birth to a son and will call him Immanuel (which means ‘God is with us’). ... 14 So the Master is going to give you a sign anyway. Watch for this: A girl who is presently a virgin will get pregnant. She'll bear a son and name him Immanuel (God-With-Us). ... 14 Therefore the Lord himself will give you a sign: behold, a virgin shall ...
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ISAIAH 7:14 KJV "Therefore the Lord himself shall give you a sign; Behold, a virgin shall conceive, and bear a son, and..."
Isaiah 7:14 KJV: Therefore the Lord himself shall give you a sign; Behold, a virgin shall conceive, and bear a son, and shall call his name Immanuel.
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Handel's Messiah - Behold, A Virgin Shall Conceive - C.S. Lewis Institute
November 2, 2023 - Jesus, the Messiah is presented to us as the Savior of the world, and He offers complete forgiveness and reconciliation to all who trust Him.
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r/AcademicBiblical on Reddit: Why is Isiah 7:14 translated "virgin will conceive"?

A Greek translation of Hebrew almah is parthenos, which can mean both "young woman" as well as "virgin."

There's a bit more detail in this thread.

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A Virgin Shall Conceive…What Does it Really Mean?
December 23, 2019 - Matthew’s account of the birth of Jesus centers around a quotation from Isaiah 7:14. Let’s look at the verse as Matthew presents it: Now the birth of Jesus Christ took place in this way…
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Matthew 1:23 "Behold, the virgin will be with child and will give birth to a son, and they will call Him Immanuel" (which means, "God with us").
Behold, the virgin will be with child and will give birth to a son, and they will call Him Immanuel (which means, God with us).
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Is Jesus Really the Virgin-Born Child in Isaiah 7?
May 14, 2020 - Is it too little for you to weary men, that you weary my God also? Therefore the LORD himself will give you [plural] a sign. Behold, the virgin shall conceive and bear a son, and shall call his name Immanuel. He shall eat curds and honey when he knows how to refuse the evil and choose the good.