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I started this new thread because this passage came up in a different thread and I didn't want to derail the OP. I apologize ahead of time for its length. If you don't want to read all this, please skip to the bottom to read my tl;dr (too long; didn't read) summary.
Admittedly, this passage from Galatians is not easy to understand and certainly prompts its readers with many questions. Which are the two covenants mentioned? What is the meaning of the allegory? What is the analogy to be drawn to Paul's listeners? What is Paul's intended message here? Everything I write here is certainly up for debate as I am simply proposing an idea to investigate and consider. I, myself, am not sure how much of it I believe to be true, but it's worth considering and praying over, nonetheless.
I believe the primary context of the letter to be about ritual circumcision for Gentile believers in the Messiah. The letter starts early on the topic of ritual circumcision (ch. 2:3ff) and concludes on the same topic (ch. 5:2ff). Thus, I will attempt to understand the passage in question (Gal. 4:21-31) with that context in mind. I'll go through verse by verse and share my thoughts.
Gal. 4:21-31 (TLV)
21. Tell me, you who want to be under Torah, don’t you understand the Torah?
[Under the Torah in what sense? Paul isn't simply talking about observing the commands of the Torah, which anyone can do regardless of their physically circumcised or uncircumcised state. "Under the Torah" here means subjecting oneself to its full authority by undergoing ritual circumcision and becoming a proselyte. This would include subjecting oneself to its punishments, as well, since the one who undergoes circumcision as a means of salvation has forsaken the Messiah's sacrifice and placed themselves under the full extent of the Torah which, without the covering of the Messiah's atoning sacrifice, ultimately results in death since no one is able to keep it perfectly.]
22. For it is written that Abraham had two sons, one by the slave woman and one by the free woman.
[Here starts the allegory. The two sons are Ishmael and Isaac, the slave woman is Hagar, and the free woman is Sarah.]
23. But one—the son by the slave woman—was born naturally; while the other—the son by the free woman—was through the promise.
[Ishmael was born as a result of human efforts apart from God, while Isaac was born as a result of the promise of God by His efforts.]
24. Now these things are being treated allegorically, for these are two covenants. One is from Mount Sinai, giving birth to slavery—this is Hagar.
[Which are the two covenants? They are the same two covenants just previously talked about in this letter: one is the covenant of promise to Abraham that he would father a great nation and all the nations would be blessed through his seed; and the other is the covenant that came 430 years later at Sinai. Hagar is allegorically the Sinai covenant, and Sarah is allegorically the Abrahamic covenant. How does the Sinai covenant give birth to slavery? Notice that this passage does not say that the Torah, which is a function of the Sinai covenant, is bondage or slavery. It says that the covenant gives birth to slavery. How so? It gives birth to slavery since it doesn't ultimately deal with the power of sin. As we read in Paul's other letters, sin was indeed alive and strong before the inauguration of the covenant in the Messiah. The Torah is said by Paul to be holy, just and good, but the Sinai covenant gives birth to bondage by not effectively dealing with the power of sin. A person succumbs to that bondage when they transgress the Torah and become subject to its penalty, which is ultimately death apart from the grace offered through the Messiah's atoning sacrifice. This implies that there were some under the Sinai covenant who were not under bondage. This would be those who had received the circumcision of the heart during that time. King David would be a good example who appears to have received this type of "heart transplant" as he was a man after God's own heart, who delighted in God's Torah and considered walking in it to be liberty. Sin has always been described throughout the OT as bondage, and freedom from that bondage as following God's Torah. You will not read in the OT that God's Torah is bondage and that freedom would be to walk outside of God's Torah, so we should be cautious about interpreting Paul in this way. The problem remains sin and the penalty of sin. God's Torah is not the problem, but a corpus of commands are ineffective on their own, as they are external to one and unable to change a person's heart. Thanks be to God that He sent His Son to die in our place, putting to death the power of sin for the believer, and putting His Torah on our transformed hearts. In this way, the new covenant is better than the old covenant, as it is built on better promises.]
25. But this Hagar is Mount Sinai in Arabia and corresponds to the present Jerusalem, for she is in slavery along with her children.
[Again, Hagar is the Sinai covenant. How is the present Jerusalem in slavery? They could have been considered to be in slavery in many different ways. First, it was an earthly kingdom as opposed to the heavenly one, so it and its children were subject to the (evil) "powers and principalities" of this world. Second, earthly Jerusalem was under oppressive Roman authority at the time. Third, the Jewish people were under corrupt religious leadership, who were not actually keeping God's Torah, but had perverted it and traded it for their own rules and regulations. In other words, earthly Jerusalem had departed from God's Torah, having transgressed it, and were under sin, with no hope having denied the Messiah's atoning sacrifice.]
26. But the Jerusalem above is free—she is our mother.
[The Jerusalem above is the heavenly New Jerusalem of the Messianic Age and world to come, as indicated by the next verse. Those who have entered into the covenant through the Messiah have attained a place in the kingdom of God and the heavenly Jerusalem. Paul says she is "our mother" because the New Jerusalem is made of both Jewish and Gentile believers (Paul and his Gentile audience).]
27. For it is written: “Rejoice, O barren woman who bears no children. Break forth and shout, you who suffer no labor pains. For more are the children of the desolate than of the one who has a husband.”
[This is from Isaiah 54:1, which prophetically references the heavenly New Jerusalem to come at the end of days. It's a very fitting reference since, in the prophecy, Isaiah depicts a ruined Jerusalem as a barren woman because her children have gone into exile (this being the Jewish people), but at the time of the final redemption the Jewish people return to her and the Gentiles join as well. This corresponds to Sarah, the barren woman who became the mother of a nation and through whom all the nations are blessed. And it beautifully follows Isaiah 53, which is an obvious prophecy of our Messiah.]
28. Now you, brothers and sisters—like Isaac, you are children of promise.
[What is Paul ultimately trying to say to his audience? His audience was Gentile believers being pressured into and considering ritual circumcision to become proselytes. The real analogy here concerns these people. Those who would attempt to merit the promise of salvation through their own efforts by ritual circumcision are analogous to Hagar, with whom Abraham tried to force by his own efforts the promise that God had given him that he would bear a child and through him all the nations would be blessed. Those who do not rely on their own efforts to merit their own salvation, but instead on God's efforts, are analogous to Sarah, through whom God delivered on His promise. This latter group of Gentiles are "children of promise" because they are, in fact, a direct fulfillment of the promise that God gave to Abraham that the nations would be blessed through his seed. They are these people of the nations who have been blessed by being allowed to enter into covenantal relationship with God through the Messiah, not having been physical descendants of Abraham.]
29. But just as at that time the one born according to the flesh persecuted the one born according to the Ruach, so it is now.
[This is referring to Ishmael, the one born according to the flesh by Abraham's own efforts, persecuting Isaac, the one born according to the Spirit and by the promise of God, not by Abraham's own efforts. Interestingly enough, there is not a very detailed account in Genesis of this persecution other than a brief mention of Ishmael "making fun" at one point (Gen. 21:9).]
30. But what does the Scripture say? “Drive out the slave woman and her son, for the son of the slave woman shall not inherit with the son” of the free woman.
[This is quoted from Gen. 21:10 when Hagar is sent out from Abraham's presence.]
31. So then, brothers and sisters, we are not children of the slave woman but of the free woman.
[The Gentiles who have been reconciled to God by faith in the Messiah are spiritual children of Abraham and his wife, Sarah. They are a direct fulfillment of the prophecy that God would bless the nations through Abraham's seed, for they are from the nations and not physically descended from Abraham, and they have come to God through the Seed that is the Messiah. But anyone attempting to pursue salvation through their own efforts by becoming proselytes through ritual circumcision, these people are removing themselves from the promise given to Abraham and placing themselves under bondage, making themselves spiritual children of Hagar who represents an attempt by human efforts to forcefully manifest the promise of God.]
TL;DR summary
This passage is ultimately about ritual circumcision. The Gentiles who are opting to become proselytes by ritual circumcision are attempting to merit their salvation by their own efforts. They are analogous to Hagar, with whom Abraham attempted by his own efforts to manifest the promise of God to be blessed with a child and to be a father to many nations which would be blessed by his Seed. The Gentiles who are not attempting to merit their salvation through ritual circumcision are the children "of the promise" given to Abraham who would come from the nations and be blessed by his Seed. They are relying on God's efforts and not their own efforts.
The Gentiles who are relying on their own efforts and undergoing ritual circumcision are putting themselves under bondage by submitting themselves from the full authority of the Torah, which includes the full extent of its punishments. They are denying the grace of God by attempting to merit their salvation and will be subject to the ultimate penalty of transgressing the Torah: death. The Gentiles who are not relying on their own efforts, but on the efforts of God, are free by their faith in the Messiah, not being subject to the ultimate penalty of the Torah since the Messiah has paid that price for their freedom from sin and death.
This does not imply that the Torah itself is bondage or that keeping the commands of the Torah places oneself "under the Torah," thus making oneself subject to its curse, which is the penalty of transgressing it. We should not desire to be "under the Torah" in this way, but should instead rely on the work of the Messiah, not our own human efforts.
Admittedly, this passage from Galatians is not easy to understand and certainly prompts its readers with many questions. Which are the two covenants mentioned? What is the meaning of the allegory? What is the analogy to be drawn to Paul's listeners? What is Paul's intended message here? Everything I write here is certainly up for debate as I am simply proposing an idea to investigate and consider. I, myself, am not sure how much of it I believe to be true, but it's worth considering and praying over, nonetheless.
I believe the primary context of the letter to be about ritual circumcision for Gentile believers in the Messiah. The letter starts early on the topic of ritual circumcision (ch. 2:3ff) and concludes on the same topic (ch. 5:2ff). Thus, I will attempt to understand the passage in question (Gal. 4:21-31) with that context in mind. I'll go through verse by verse and share my thoughts.
Gal. 4:21-31 (TLV)
21. Tell me, you who want to be under Torah, don’t you understand the Torah?
[Under the Torah in what sense? Paul isn't simply talking about observing the commands of the Torah, which anyone can do regardless of their physically circumcised or uncircumcised state. "Under the Torah" here means subjecting oneself to its full authority by undergoing ritual circumcision and becoming a proselyte. This would include subjecting oneself to its punishments, as well, since the one who undergoes circumcision as a means of salvation has forsaken the Messiah's sacrifice and placed themselves under the full extent of the Torah which, without the covering of the Messiah's atoning sacrifice, ultimately results in death since no one is able to keep it perfectly.]
22. For it is written that Abraham had two sons, one by the slave woman and one by the free woman.
[Here starts the allegory. The two sons are Ishmael and Isaac, the slave woman is Hagar, and the free woman is Sarah.]
23. But one—the son by the slave woman—was born naturally; while the other—the son by the free woman—was through the promise.
[Ishmael was born as a result of human efforts apart from God, while Isaac was born as a result of the promise of God by His efforts.]
24. Now these things are being treated allegorically, for these are two covenants. One is from Mount Sinai, giving birth to slavery—this is Hagar.
[Which are the two covenants? They are the same two covenants just previously talked about in this letter: one is the covenant of promise to Abraham that he would father a great nation and all the nations would be blessed through his seed; and the other is the covenant that came 430 years later at Sinai. Hagar is allegorically the Sinai covenant, and Sarah is allegorically the Abrahamic covenant. How does the Sinai covenant give birth to slavery? Notice that this passage does not say that the Torah, which is a function of the Sinai covenant, is bondage or slavery. It says that the covenant gives birth to slavery. How so? It gives birth to slavery since it doesn't ultimately deal with the power of sin. As we read in Paul's other letters, sin was indeed alive and strong before the inauguration of the covenant in the Messiah. The Torah is said by Paul to be holy, just and good, but the Sinai covenant gives birth to bondage by not effectively dealing with the power of sin. A person succumbs to that bondage when they transgress the Torah and become subject to its penalty, which is ultimately death apart from the grace offered through the Messiah's atoning sacrifice. This implies that there were some under the Sinai covenant who were not under bondage. This would be those who had received the circumcision of the heart during that time. King David would be a good example who appears to have received this type of "heart transplant" as he was a man after God's own heart, who delighted in God's Torah and considered walking in it to be liberty. Sin has always been described throughout the OT as bondage, and freedom from that bondage as following God's Torah. You will not read in the OT that God's Torah is bondage and that freedom would be to walk outside of God's Torah, so we should be cautious about interpreting Paul in this way. The problem remains sin and the penalty of sin. God's Torah is not the problem, but a corpus of commands are ineffective on their own, as they are external to one and unable to change a person's heart. Thanks be to God that He sent His Son to die in our place, putting to death the power of sin for the believer, and putting His Torah on our transformed hearts. In this way, the new covenant is better than the old covenant, as it is built on better promises.]
25. But this Hagar is Mount Sinai in Arabia and corresponds to the present Jerusalem, for she is in slavery along with her children.
[Again, Hagar is the Sinai covenant. How is the present Jerusalem in slavery? They could have been considered to be in slavery in many different ways. First, it was an earthly kingdom as opposed to the heavenly one, so it and its children were subject to the (evil) "powers and principalities" of this world. Second, earthly Jerusalem was under oppressive Roman authority at the time. Third, the Jewish people were under corrupt religious leadership, who were not actually keeping God's Torah, but had perverted it and traded it for their own rules and regulations. In other words, earthly Jerusalem had departed from God's Torah, having transgressed it, and were under sin, with no hope having denied the Messiah's atoning sacrifice.]
26. But the Jerusalem above is free—she is our mother.
[The Jerusalem above is the heavenly New Jerusalem of the Messianic Age and world to come, as indicated by the next verse. Those who have entered into the covenant through the Messiah have attained a place in the kingdom of God and the heavenly Jerusalem. Paul says she is "our mother" because the New Jerusalem is made of both Jewish and Gentile believers (Paul and his Gentile audience).]
27. For it is written: “Rejoice, O barren woman who bears no children. Break forth and shout, you who suffer no labor pains. For more are the children of the desolate than of the one who has a husband.”
[This is from Isaiah 54:1, which prophetically references the heavenly New Jerusalem to come at the end of days. It's a very fitting reference since, in the prophecy, Isaiah depicts a ruined Jerusalem as a barren woman because her children have gone into exile (this being the Jewish people), but at the time of the final redemption the Jewish people return to her and the Gentiles join as well. This corresponds to Sarah, the barren woman who became the mother of a nation and through whom all the nations are blessed. And it beautifully follows Isaiah 53, which is an obvious prophecy of our Messiah.]
28. Now you, brothers and sisters—like Isaac, you are children of promise.
[What is Paul ultimately trying to say to his audience? His audience was Gentile believers being pressured into and considering ritual circumcision to become proselytes. The real analogy here concerns these people. Those who would attempt to merit the promise of salvation through their own efforts by ritual circumcision are analogous to Hagar, with whom Abraham tried to force by his own efforts the promise that God had given him that he would bear a child and through him all the nations would be blessed. Those who do not rely on their own efforts to merit their own salvation, but instead on God's efforts, are analogous to Sarah, through whom God delivered on His promise. This latter group of Gentiles are "children of promise" because they are, in fact, a direct fulfillment of the promise that God gave to Abraham that the nations would be blessed through his seed. They are these people of the nations who have been blessed by being allowed to enter into covenantal relationship with God through the Messiah, not having been physical descendants of Abraham.]
29. But just as at that time the one born according to the flesh persecuted the one born according to the Ruach, so it is now.
[This is referring to Ishmael, the one born according to the flesh by Abraham's own efforts, persecuting Isaac, the one born according to the Spirit and by the promise of God, not by Abraham's own efforts. Interestingly enough, there is not a very detailed account in Genesis of this persecution other than a brief mention of Ishmael "making fun" at one point (Gen. 21:9).]
30. But what does the Scripture say? “Drive out the slave woman and her son, for the son of the slave woman shall not inherit with the son” of the free woman.
[This is quoted from Gen. 21:10 when Hagar is sent out from Abraham's presence.]
31. So then, brothers and sisters, we are not children of the slave woman but of the free woman.
[The Gentiles who have been reconciled to God by faith in the Messiah are spiritual children of Abraham and his wife, Sarah. They are a direct fulfillment of the prophecy that God would bless the nations through Abraham's seed, for they are from the nations and not physically descended from Abraham, and they have come to God through the Seed that is the Messiah. But anyone attempting to pursue salvation through their own efforts by becoming proselytes through ritual circumcision, these people are removing themselves from the promise given to Abraham and placing themselves under bondage, making themselves spiritual children of Hagar who represents an attempt by human efforts to forcefully manifest the promise of God.]
TL;DR summary
This passage is ultimately about ritual circumcision. The Gentiles who are opting to become proselytes by ritual circumcision are attempting to merit their salvation by their own efforts. They are analogous to Hagar, with whom Abraham attempted by his own efforts to manifest the promise of God to be blessed with a child and to be a father to many nations which would be blessed by his Seed. The Gentiles who are not attempting to merit their salvation through ritual circumcision are the children "of the promise" given to Abraham who would come from the nations and be blessed by his Seed. They are relying on God's efforts and not their own efforts.
The Gentiles who are relying on their own efforts and undergoing ritual circumcision are putting themselves under bondage by submitting themselves from the full authority of the Torah, which includes the full extent of its punishments. They are denying the grace of God by attempting to merit their salvation and will be subject to the ultimate penalty of transgressing the Torah: death. The Gentiles who are not relying on their own efforts, but on the efforts of God, are free by their faith in the Messiah, not being subject to the ultimate penalty of the Torah since the Messiah has paid that price for their freedom from sin and death.
This does not imply that the Torah itself is bondage or that keeping the commands of the Torah places oneself "under the Torah," thus making oneself subject to its curse, which is the penalty of transgressing it. We should not desire to be "under the Torah" in this way, but should instead rely on the work of the Messiah, not our own human efforts.
