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.
There are two ways to think about the grace of God: One is to look at yourself and see how sinful you were and say, “God’s grace must be vast—it must be huge as space to forgive such a sinner as I am.” That’s one way and that’s a good way—and probably that’s the most popular way.
But there’s another way to think of the grace of God. Think of it as the way God is—God being like God. And when God shows grace to a sinner He isn’t being dramatic; He’s acting like God. He’ll never act any other way but like God. On the other hand, when that man whom justice has condemned turns his back on the grace of God in Christ and refuses to allow himself to be rescued, then the time comes when God must judge the man. And when God judges the man He acts like Himself in judging the man. When God shows love to the human race He acts like Himself. When God shows judgment to “the angels which kept not their first estate” (Jude 6), He acts like Himself.
Always God acts in conformity with the fullness of His own wholly perfect, symmetrical nature. AOG106
Father, I’m thankful that You always act like Yourself—with grace and justice. Your constancy produces great peace within me. Amen. 
the apostate angels
And angels who did not keep their own domain, but abandoned their proper abode, He has kept in eternal bonds under darkness for the judgment of the great day, (6)
The second example that Jude gave was that of apostate angels. The fact that these angels are not specifically identified indicates that Jude assumed his audience was already familiar with the details of their extraordinary defection.
Commentators have offered three main views as to the identity of these angels. Some argue that Jude’s reference is to an episode his readers knew nothing about. But that does not fit the larger context in which, as noted above, Jude reminded his readers of things they already knew (cf. v. 5). Thus one has to assume that Jude wrote of an Old Testament account that was generally familiar to his audience.
Others assert that Jude referred to the original fall of Satan (Isa. 14:12–15; Ezek. 28:12–17; cf. Luke 10:18; Rev. 12:7–10). That is a possible interpretation, but it fails to explain Jude’s mention of eternal bonds, which does not apply to the current status of Satan and demons. The apostle Peter correctly wrote that the devil “prowls around like a roaring lion, seeking someone to devour” (1 Peter 5:8; cf. Job 1:6–7). Therefore it is unlikely that Jude is referring to Satan’s fall.
A third and most plausible viewpoint is that Jude referred to an extraordinarily heinous infraction by some of the fallen angels. That sin, recorded in the Old Testament (Gen. 6:1–4), was so severe that God placed the offending demons in chains to prevent them from committing such perversity ever again. (For more discussion of the sin committed by those angels, see the comments on 2 Peter 2:4 in chapter 6 of this volume and the lengthier section in John MacArthur, 1 Peter, MacArthur New Testament Commentary [Chicago: Moody, 2004], 209–16.)
Peter said they sinned, whereas Jude described two closely related aspects of the fallen angels’ sin. First, they did not keep their own domain. Instead of staying in their own realm of authority given by God, they went outside it. Second, they abandoned their proper abode. With Lucifer they rebelled against their created role and place in heaven (cf. Isa. 14:12, nkjv). When God expelled them from heaven for that rebellion (cf. Rev. 12:4, 9), some continued their downward fall to the point of taking masculine human form and cohabitating with human women to produce a generation of demon-influenced, thoroughly corrupt children (cf. Gen. 6:11–13). God sent those particular apostate angels (demons) to a place under darkness for the judgment of the great day. Peter wrote that God “committed them to pits of darkness, reserved for judgment” (2 Peter 2:4).
6 The second example of rebellion and apostasy is the angels who sinned. All we know about them for certain is that they did not keep the domain that was assigned to them, they abandoned their own abode, and they are now restrained in everlasting chains under darkness for their final judgment.
It seems from Scripture that there have been at least two apostasies of angels. One was when Lucifer fell and presumably involved a host of other angelic beings in his rebellion. These fallen angels are not bound at the present time. The devil and his demons are actively promoting war against the Lord and His people.
The other apostasy of angels is the one referred to by Jude and also by Peter (2 Pet. 2:4). There is considerable difference of opinion among Bible students as to what event is referred to here. What we suggest is a personal viewpoint, not a dogmatic assertion of fact.
We believe that Jude is referring to what is recorded in Genesis 6:1–7. The sons of God left their proper estate as angelic beings, came down to the earth in human form, and married the daughters of men. This marital union was contrary to God’s order and an abomination to Him. There may be a suggestion in verse 4 that these unnatural marriages produced offspring of tremendous strength and wickedness. Whether or not this is true, it is clear that God was exceedingly displeased with the wickedness of man at this time and determined to destroy the earth with a flood.
There are three objections to this view: (1) The passage in Genesis does not mention angels, but only “sons of God.” (2) Angels are sexless. (3) Angels do not marry.
It is true that angels are not specifically mentioned but it is also true that the term “sons of God” does refer to angels in Semitic languages (see Job 1:6; 2:1).
There is no Bible statement that angels are sexless. Angels sometimes appeared on earth in human form, having human parts and appetites (Gen. 18:2, 22; compare 19:1, 3–5.
The Bible does not say that angels do not marry but only that in heaven they neither marry nor give in marriage (Matt. 22:30).
Whatever historical incident may lie behind verse 6, the important point is that these angels abandoned the sphere which God had marked out for them and are now in … chains and in darkness until the time when they will receive their final sentence to perdition.
The Fallen Angels (6)
6 The angels are said to have “abandoned” their heavenly home. (Note the prefix apo– in the participle apolipontas, denoting movement away.) They fell from a domain of divine liberty and light to imprisonment and darkness. Jude’s readers are to be mindful of the lesson of the angels: punishment is proportionate to privilege. In heavenly realms the angels were exposed to great light; now they are consigned to the gloom of darkness. Having chosen not to “keep” their unique and exalted status, they are consequently being “kept” in chains of darkness awaiting a fate—“the great Day”—which should cause humans to shudder. Like Israel of old, they departed from their “allotted” place. Apostasy in the Christian community has both earthly and heavenly antecedents.
Neither the OT nor the NT makes any explicit statements as to the fall of the rebellious angels. The NT implies at most that Satan, a fallen angel chief among many (cf. Eph 2:2), was hurled down (Lk 10:18; Jn 12:31; Rev 12:4, 7, 9, 10), yet it gives no clear time or explanation for the fall. Some hold Jesus’ words in Luke 10:18 to refer to an original fall; others interpret the statement to be a dramatic way of expressing Satan’s certain ruin (so G. Aulen, Christus Victor [New York: Macmillan, 1956], 111). Still others view the fall as coinciding with Jesus’ earthly ministry (so G. B. Caird, Principalities and Powers [Oxford: Clarendon, 1965], 31).
Virtually all commentary—past and present—has related Jude 6 (and 2 Pe 2:4) to Genesis 6:1–4 in some way or another. This interpretation of “the sons of God” (Ge 6:2), following the lead of Clement of Alexandria, is largely due to two reasons: (1) a mistaken linking of the angels in Jude 6 with Sodom and Gomorrah in v. 7 and (2) the association of demons with Genesis 6:1–4 that began to emerge in second-century BC Jewish interpretation. In 1 Enoch (second–first century BC?), for example, we find perhaps the most elaborate expansion of this connection between the angels’ fall and sexual promiscuity.
The sin of the angels, though veiled to humans, was very real. The point of Jude’s witness, however, is not the precise nature of their sin. Rather, the angels of v. 6, mentioned parenthetically, share something in common with Israel of v. 5 and the cities of the plain in v. 7, namely, a radical disobedience and total disenfranchisement. The reader must be careful to note what Jude, in his borrowing of apocalyptic motifs, stresses and what he omits. Contrary to the view of numerous commentators, there is nothing concerning angels in Genesis 6 that is mentioned in Jude; rather, the conceptualization of the angelic realm in Jude is simply an extension of that which emerged during the intertestamental era. The Jewish apocalypticist was inclined to assimilate pagan mythology into his conceptualization of the angelic world. Biblical writers, on the other hand, by nature were nonmythological, i.e., they wrote from a divine revelatory and prophetic posture, even when they utilized the apocalyptic literary mode for their own purposes.
Jude employs apocalyptic motifs without necessarily embracing Jewish apocalyptic theology. The central point of his illustration involving the angels is the fact that they were dispossessed, not how or specifically why they were dispossessed. This basic interpretive premise is confirmed by the grammar and syntax of v. 6. The issue at hand is apostasy, not fornication (see my Literary Strategy in the Epistle of Jude, 108–16). All three examples in Jude 5–7 underscore the fact of enduring loss. Any speculation as to the particular nature of the sins of the angels, intriguing as it may be, is of secondary importance. The point of Jude’s allusion to the angels is that they exercised their free will wrongly—to their own discredit.
6 While angels in the OT figure prominently in certain historical narratives, during and following Israel’s exile they acquire increasing importance and a more clearly defined function (e.g., Eze 9:2.; 40:3.; 43:6.; Da 3:28; 4:13; 6:22; 7:16; 8:13; 10:5–6.; 12:1; Zec 1:8; 2:1; 3:1 4:1; 5:5; 6:4). In Jewish intertestamental literature, the depiction of angels becomes far more systematic, with a particular number having their names and functions expressly stated, a prime example being 1 Enoch.
6 Corresponding typology to the fallen angels of Jude might well be drawn from several prophetic oracles in the OT—oracles serving as graphic illustrations of fall or ruin: Isaiah 14:5–23, a taunt against the king of Babylon; Isa 24:21–22, a symbolic representation of Yahweh’s judgment; and Ezekiel 28:1–19, a prophetic funeral dirge against the king of Tyre. The oracles in Isaiah 14 and Ezekiel 28 reflect, as in Jude, utter fall from glory. Significantly, several elements are present in all three sources: (1) there is a conspicuously abrupt transition from the earthly plane to the heavenly; (2) a correlation is made between the earthly and heavenly realms; and (3) the objects of condemnation all tumble from the heavens as “stars” (cf. v. 13). Falling from glory, whether it is an arrogant king or those to whom truth has been committed, has an extraordinary antecedent in the heavenly realm.
6 The imprisonment of spirits, undefined in the OT, is a prominent theme in Jewish apocalyptic literature (notably in 1 En.; 2 Bar.; Jub.) and surfaces in the book of Revelation. Within the apocalyptic tradition, a frequent pattern tends to emerge: (1) war erupts in heaven, often depicted in astral terms; followed by (2) a spilling over of this rebellion to earth; culminating in (3) ultimate vindication and punishment by the king of heaven (see P. D. Hanson, “Rebellion in Heaven, Azazel, and Euhemeristic Heroes in 1 Enoch 6–11,” JBL 96 : 208).
 Tozer, A. W., & Eggert, R. (2015). Tozer on the almighty god: a 365-day devotional. Chicago, IL: Moody Publishers.
 MacArthur, J. F., Jr. (2005). 2 Peter and Jude (pp. 164–165). Chicago: Moody Publishers.
 MacDonald, W. (1995). Believer’s Bible Commentary: Old and New Testaments. (A. Farstad, Ed.) (p. 2341). Nashville: Thomas Nelson.
 Charles, D. J. (2006). Jude. In T. Longman III & D. E. Garland (Eds.), The Expositor’s Bible Commentary: Hebrews–Revelation (Revised Edition) (Vol. 13, pp. 554–555). Grand Rapids, MI: Zondervan.