And the angels which kept not their first estate, but left their own habitation, he hath reserved in everlasting chains under darkness unto the judgment of the great day.

And angels that kept not their own principality, but left their proper habitation, he hath kept in everlasting bonds under darkness unto the judgment of the great day.

And the angels who kept not their principality, but forsook their own habitation, he hath reserved under darkness in everlasting chains, unto the judgment of the great day.

And angels who had not kept their own original state, but had abandoned their own dwelling, he keeps in eternal chains under gloomy darkness, to the judgment of the great day;

And the angels who kept not their first state, but left their own habitation, he hath reserved in everlasting chains under darkness to the judgment of the great day.

messengers also, those who did not keep their own principality, but did leave their proper dwelling, to a judgment of a great day, in bonds everlasting, under darkness He hath kept,

And angels - those who did not keep the position originally assigned to them, but deserted their own proper abode - He reserves in everlasting bonds, in darkness, in preparation for the judgement of the great day.

But Adoni-zedek went in flight; and they went after him and overtook him, and had his thumbs and his great toes cut off.

And truly, the Angels, who did not keep to their first place, but instead abandoned their own domiciles, he has reserved with perpetual chains under darkness, unto the great day of judgment.

and that even those angels, who did not keep to their appointed spheres, but left their proper homes, have been kept by him for the judgment of the great day in everlasting chains and black darkness.

Angelos vero qui principatum (vel, initium) suum non servaverant, sed reliquerant suum domicilium, judicium magnae diei vinculis aeternis sub caligine servavit.

And the angels. This is an argument from the greater to the less; for the state of angels is higher than ours; and yet God punished their defection in a dreadful manner. He will not then forgive our perfidy, if we depart from the grace unto which he has called us. This punishment, inflicted on the inhabitants of heaven, and on such superior ministers of God, ought surely to be constantly before our eyes, so that we may at no time be led to despise God's grace, and thus rush headlong into destruction. The word arche in this place, may be aptly taken for beginning as well as for principality or dominion. For Jude intimates that they suffered punishment, because they had despised the goodness of God and deserted their first vocation. And there follows immediately an explanation, for he says that they had left their own habitation; for, like military deserters, they left the station in which they had been placed. We must also notice the atrocity of the punishment which the Apostle mentions. They are not only free spirits but celestial powers; they are now held bound by perpetual chains. They not only enjoyed the glorious light of God, but his brightness shone forth in them, so that from them, as by rays, it spread over all parts of the universe; now they are sunk in darkness. But we are not to imagine a certain place in which the devils are shut up, for the Apostle simply intended to teach us how miserable their condition is, since the time they apostatized and lost their dignity. For wherever they go, they drag with them their own chains, and remain involved in darkness. Their extreme punishment is in the meantime, deferred until the great day comes.

And the angels which kept not their first estate - A second case denoting that the wicked would be punished. Compare the notes, 2-Peter 2:4. The word rendered "estate" (ἀρχὴν archēn) is, in the margin, "principality." The word properly means, "beginning, commencement;" and then that which surpasses others, which is "first," etc., in point of rank and honor; or pre-eminence, priority, precedence, princedom. Here it refers to the rank and dignity which the angels had in heaven. That rank or pre-eminence they did not keep, but fell from it. On the word used here, compare Ephesians 1:2; Ephesians 3:10; Colossians 2:10, as applied to angels; 1-Corinthians 15:24; Ephesians 6:12; Colossians 2:15, as applied to demons.
But left their own habitation - To wit, according to the common interpretation, in heaven. The word rendered "habitation" (οἰκητήριον oikētērion) occurs nowhere else in the New Testament. It means here that heaven was their native abode or dwelling-place. They left it by sin; but the expression here would seem possibly to mean that they became "dissatisfied" with their abode, and voluntarily preferred to change it for another. If they did become thus dissatisfied, the cause is wholly unknown, and conjecture is useless. Some of the later Jews supposed that they relinquished heaven out of love for the daughters of men - "Robinson."
He hath reserved in everlasting chains - See the notes, 2-Peter 2:4. Peter says, "chains of darkness;" that is, the darkness encompasses them "as" chains. Jude says that those chains are "everlasting," (δεσμοῖς ἀΐ́δίοις desmois aidios. Compare Romans 1:20, "his eternal power and Godhead." The word does not elsewhere occur. It is an appropriate word to denote that which is eternal; and no one can doubt that if a Greek wished to express that idea, this would be a proper word to use. The sense is, that that deep darkness always endures; there is no intermission; no light; it will exist forever. This passage in itself does not prove that the punishment of the rebel angels will be eternal, but merely that they are kept in a dark prison in which there is no light, and which is to exist for ever, with reference to the final trial. The punishment of the rebel angels after the judgment is represented as an everlasting fire, which has been prepared for them and their followers, Matthew 25:41.

The angels which kept not their first estate - Την ἑαυτων αρχην Their own principality. The words may be understood of their having invaded the office or dignity of some others, or of their having by some means forfeited their own. This is spoken of those generally termed the fallen angels; but from what they fell, or from what cause or for what crime, we know not. It is generally thought to have been pride; but this is mere conjecture. One thing is certain; the angels who fell must have been in a state of probation, capable of either standing or falling, as Adam was in paradise. They did not continue faithful, though they knew the law on which they stood; they are therefore produced as the second example.
But left their own habitation - This seems to intimate that they had invaded the office and prerogatives of others, and attempted to seize on their place of residence and felicity.
He hath reserved in everlasting chains - That is, in a state of confinement from which they cannot escape.
Under darkness - Alluding probably to those dungeons or dark cells in prisons where the most flagitious culprits were confined.
The judgment of the great day, - The final judgment, when both angels and men shall receive their eternal doom. See on 2-Peter 2:4 (note). In Sohar Exod., fol. 8, c. 32: "Rabbi Isaac asked: Suppose God should punish any of his heavenly family, how would he act? R. Abba answered: He would send them into the flaming river, take away their dominion, and put others in their place." Some suppose that the saints are to occupy the places from which these angels, by transgression, fell.

(5) And the angels which kept not their first estate, but left their own habitation, he hath reserved in everlasting chains under darkness unto the judgment of the great day.
(5) The fall of the angels was most severely punished, how much more then will the Lord punish wicked and faithless men?

And the angels which kept not their first estate,.... Or "principality"; that holy, honourable, and happy condition, in which they were created; for they were created in perfect holiness and righteousness, stood in the relation of sons to God, and were, for the lustre of their nature, comparable to the morning stars; they were among the thrones, dominions, principalities, and powers; were a superior rank of creatures to men, and who beheld the face, and enjoyed the presence of God; but this estate they kept not, for being mutable creatures, one of them first sinning, the rest were drawn into it by him, and so were not what they were before, nor in the same estate, or place:
but left their own habitation; by attempting to rise higher; or by quitting their station and posts of honour, being unwilling to be subject to God, and especially to the Son of God, who was to assume human nature, and in it be above them, which they could not bear; and by gathering together in a body, in another place, with Satan at the head of them; though this may be considered as a part of their punishment, and they may be said to do what they were forced to; for they were drove out of their native habitation, heaven; they were turned out of it, and cast down to hell; see 2-Peter 2:4. And this their habitation, which they left, or fell from, or they were cast out of, is by the Jews frequently called the place of their holiness, or their holy place (g),
He hath reserved in everlasting chains, under darkness; by these "everlasting chains" may be meant the power and providence of God over them, which always abide upon them; or their sins, and the guilt of them upon their consciences, under which they are continually held; or the decrees and purposes of God concerning their final punishment and destruction, which are immutable and irreversible, and from which there is no freeing themselves:, the phrase, under darkness, may refer to the chains, as in 2-Peter 2:4; where they are called "chains of darkness"; either because the power, providence, and purposes of God are invisible; so the Syriac version reads, "in unknown chains"; or because horror and black despair are the effects of sin, and its guilt, with which their consciences are continually filled: or it may denote the place and state where they are, either in the darkness of the air, or in the dark parts of the earth, or in hell, where is utter darkness, even blackness of darkness; or that they are under the power of sin, which is darkness, and without the light of God's countenance, or any spiritual knowledge, or comfort: and they are "reserved" in these chains, and under this darkness; or "in prison", as the Arabic version renders it; which denotes the custody of them, and their continuance in it, in which they are kept by Jesus Christ, who can bind and loose Satan at his pleasure; and it shows that they are not as yet in full torment, but are like malefactors that are kept in prison, until the assize comes: so these are laid in chains, and kept in custody
unto the judgment of the great day; that is, the future and last "judgment" of men and devils, which is certain, and will be universal, and executed with the strictest justice: this is called "a day", which is fixed by God, though unknown to men and angels; and because of the evidence and quick dispatch of things, the matters judged will be as clear as the day, and finished at once; and a great one, for the Judge will appear in great glory; great things will be done, the dead will be raised, and all nations will be gathered together, and the process will be with great solemnity; the thrones will be set, the books opened, the several sentences pronounced, and, all punctually executed; the judgment of the great day is the same the Jews call , "the day of the great judgment" (h). This account shows the imprisoned state of the devils, that they are not their own lords, and cannot do as they would; they are under restraints, and in chains, and not to be feared; which must be a great mortification to their proud and malicious spirits: and since this is the case of fallen angels, what severity may be expected from God against the opposers of the truths of the Gospel?
(g) Yalkut Simeoni, par. 2. fol. 73. 1. Pirke Eliezer, c. 14, 22, 27. Zohar in Genesis. fol. 28. 1. & Sepher Bahir in ib. fol. 27. 3. (h) Targum in Psal. l. 3.

(2-Peter 2:4.)
kept not their first estate--Vulgate translates, "their own principality," which the fact of angels being elsewhere called "principalities," favors: "their own" implies that, instead of being content with the dignity once for all assigned to them under the Son of God, they aspired higher. ALFORD thinks the narrative in Genesis 6:2 is alluded to, not the fall of the devil and his angels, as he thinks "giving themselves over to fornication" (Jde 1:7) proves; compare Greek, "in like manner to these," namely, to the angels (Jde 1:6). It seems to me more natural to take "sons of God" (Genesis 6:2) of the Sethites, than of angels, who, as "spirits," do not seem capable of carnal connection. The parallel, 2-Peter 2:4, plainly refers to the fall of the apostate angels. And "in like manner to these," Jde 1:7, refers to the inhabitants of Sodom and Gomorrah, "the cities about them" sinning "in like manner" as "they" did [ESTIUS and CALVIN]. Even if Greek "these," Jde 1:7, refer to the angels, the sense of "in like manner as these" will be, not that the angels carnally fornicated with the daughters of men, but that their ambition, whereby their affections went away from God and they fell, is in God's view a sin of like kind spiritually as Sodom's going away from God's order of nature after strange flesh; the sin of the apostate angels after their kind is analogous to that of the human Sodomites after their kind. Compare the somewhat similar spiritual connection of whoremongers and covetousness. The apocryphal book of Enoch interprets Genesis 6:2 as ALFORD. But though Jude accords with it in some particulars, it does not follow that he accords with it in all. The Hebrews name the fallen angels Aza and Azael.
left--on their own accord.
their own--Greek, "their proper."
habitation--heaven, all bright and glorious, as opposed to the "darkness" to which they now are doomed. Their ambitious designs seem to have had a peculiar connection with this earth, of which Satan before his fall may have been God's vicegerent, whence arises his subsequent connection with it as first the Tempter, then "the prince of this world."
reserved--As the Greek is the same, and there is an evident reference to their having "kept not their first estate," translate, "He hath kept." Probably what is meant is, He hath kept them in His purpose; that is their sure doom; moreover, as yet, Satan and his demons roam at large on the earth. An earnest of their doom is their having been cast out of heaven, being already restricted to "the darkness of this present world," the "air" that surrounds the earth, their peculiar element now. They lurk in places of gloom and death, looking forward with agonizing fear to their final torment in the bottomless pit. He means not literal chains and darkness, but figurative in this present world where, with restricted powers and liberties, shut out from heaven, they, like condemned prisoners, await their doom.

And the angels, who kept not their first dignity - Once assigned them under the Son of God. But voluntarily left their own habitation - Then properly their own, by the free gift of God. He reserved - Delivered to be kept. In everlasting chains under darkness - O how unlike their own habitation! When these fallen angels came out of the hands of God, they were holy; else God made that which was evil: and being holy, they were beloved of God; else he hated the image of his own spotless purity. But now he loves them no more; they are doomed to endless destruction. (for if he loved them still, he would love what is sinful:) and both his former love, and his present righteous and eternal displeasure towards the same work of his own hands, are because he changeth not; because he invariably loveth righteousness, and hateth iniquity. 2-Peter 2:4.