The interpretation timeline
Jude 1:6 Douay-Rheims

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.

A.D. 100 – 1871 12 witnesses 13 excerpts

Patristic

before A.D. 750
100
A.D.
c. A.D. 37–100
“For many angels of God accompanied with women, and begat sons that proved unjust, and despisers of all that was good, on account of the confidence they had in their own strength; for the tradition is, that these men did what resembled the acts of those whom the Grecians call giants. But Noah was very uneasy at what they did; and being displeased at their conduct, persuaded them to change their dispositions and their acts for the better: but seeing they did not yield to him, but were slaves to their wicked pleasures, he was afraid they would kill him, together with his wife and children, and those they had married; so he departed out of that land.”
Source
165
A.D.
Justin Martyr Patristic
A.D. 100–165
“God, when He had made the whole world, and subjected things earthly to man, and arranged the heavenly elements for the increase of fruits and rotation of the seasons, and appointed this divine law-for these things also He evidently made for man-committed the care of men and of all things under heaven to angels whom He appointed over them. But the angels transgressed this appointment, and were captivated by love of women, and begat children who are those that are called demons; and besides, they afterwards subdued the human race to themselves, partly by magical writings, and partly by fears and the punishments they occasioned, and partly by teaching them to offer sacrifices, and incense, and libations, of which things they stood in need after they were enslaved by lustful passions; and among men they sowed murders, wars, adulteries, intemperate deeds, and all wickedness. Whence also the poets and mythologists, not knowing that it was the angels and those demons who had been begotten by them that did these things to men, and women, and cities, and nations, which they related, ascribed them to god himself, and to those who were accounted to be his very offspring, and to the offspring of those who were called his brother), Neptune and Pluto, and to the children again of these their offspring. For whatever name each of the angels had given to himself and his children, by that name they called them.”
Source
202
A.D.
Irenaeus Patristic
c. A.D. 130–202
“Since the Son of God is always one and the same, He gives to those who believe on Him a well of water [springing up] to eternal life, but He causes the unfruitful fig-tree immediately to dry up; and in the days of Noah He justly brought on the deluge for the purpose of extinguishing that most infamous race of men then existent, who could not bring forth fruit to God, since the angels that sinned had commingled with them, and [acted as He did] in order that He might put a check upon the sins of these men, but [that at the same time] He might preserve the archetype, the formation of Adam. And it was He who rained fire and brimstone from heaven, in the days of Lot, upon Sodom and Gomorrah, "an example of the righteous judgment of God," that all may know, "that every tree that bringeth not forth good fruit shall be cut down, and cast into the fire."”
Source
215
A.D.
c. A.D. 150–215
“To which also we shall add, that the angels who had obtained the superior rank, having sunk into pleasures, told to the women the secrets which had come to their knowledge; while the rest of the angels concealed them, or rather, kept them against the coming of the Lord.”
“"But the angels," he says, "that kept not their own pre-eminence," that, namely, which they received through advancement, "but left their own habitation," meaning, that is, the heaven and the stars, became, and are called apostates. "He hath reserved these to the judgment of the great day, in chains, under darkness." He means the place near the earth, that is, the dark air. Now he called "chains" the loss of the honour in which they had stood, and the lust of feeble things; since, bound by their own lust, they cannot be converted. "As Sodom and Gomorrha," he says.”
Source
220
A.D.
Tertullian Patristic
c. A.D. 150–220
“For they, withal, who instituted them are assigned, under condemnation, to the penalty of death — those angels, to wit, who rushed from heaven on the daughters of men; so that this ignominy also attaches to woman. For when to an age much more ignorant (than ours) they had disclosed certain well-concealed material substances, and several not well-revealed scientific arts — if it is true that they had laid bare the operations of metallurgy, and had divulged the natural properties of herbs, and had promulgated the powers of enchantments, and had traced out every curious art, even to the interpretation of the stars — they conferred properly and as it were peculiarly upon women that instrumental mean of womanly ostentation, the radiances of jewels wherewith necklaces are variegated, and the circlets of gold wherewith the arms are compressed, and the medicaments of orchil with which wools are colored, and that black powder itself wherewith the eyelids and eyelashes are made prominent. What is the quality of these things may be declared meantime, even at this point, from the quality and condition of their teachers: in that sinners could never have either shown or supplied anything conducive to integrity, unlawful lovers anything conducive to chastity, renegade spirits anything conducive to the fear of God. If (these things) are to be called teachings, ill masters must of necessity have taught ill; if as wages of lust, there is nothing base of which the wages are honourable. But why was it of so much importance to show these things as well as to confer them? Was it that women, without material causes of splendour, and without ingenious contrivances of grace, could not please men, who, while still unadorned, and uncouth and — so to say — crude and rude, had moved (the mind of) angels? Or was it that the lovers would appear sordid and — through gratuitous use — contumelious, if they had conferred no (compensating) gift on the women who had been enticed into connubial connection with them? But these questions admit of no calculation. Women who possessed angels (as husbands) could desire nothing more; they had, forsooth, made a grand match! Assuredly they who, of course, did sometimes think whence they had fallen, and, after the heated impulses of their lusts, looked up toward heaven, thus requited that very excellence of women, natural beauty, as (having proved) a cause of evil, in order that their good fortune might profit them nothing; but that, being turned from simplicity and sincerity, they, together with (the angels) themselves, might become offensive to God. Sure they were that all ostentation, and ambition, and love of pleasing by carnal means, was displeasing to God. And these are the angels whom we are destined to judge: these are the angels whom in baptism we renounce: these, of course, are the reasons why they have deserved to be judged by man. What business, then, have their things with their judges? What commerce have they who are to condemn with them who are to be condemned? The same, I take it, as Christ has with Belial. With what consistency do we mount that (future) judgment-seat to pronounce sentence against those whose gifts we (now) seek after? For you too, (women as you are,) have the self-same angelic nature promised as your reward, the self-same sex as men: the self-same advancement to the dignity of judging, does (the Lord) promise you. Unless, then, we begin even here to pre-judge, by pre-condemning their things, which we are hereafter to condemn in themselves, they will rather judge and condemn us.”
Source

Post-Reformation

c. 1650 – 1900
1771
A.D.
John Gill Reformed
1697–1771
“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 Pe2 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 Pe2 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 Gen. fol. 28. 1. & Sepher Bahir in ib. fol. 27. 3. (h) Targum in Psal. l. 3.”
Source
1832
A.D.
Adam Clarke Methodist
1762–1832
“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 Pe2 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.”
Source
1849
A.D.
1774–1849
“Principality. That is, the state in which they were first created, their original dignity. (Challoner) — Having given themselves over to [7] fornication, or to excessive uncleanness. — Going after other flesh, and seeking unnatural lusts, with those of the same sex. (Witham) — Impurity punished by fire and sulphur. Fire is a punishment proportioned to the criminal passion of the voluptuous. That of Sodom was most dreadful, but then it was of short duration. There is another fire that will never be extinguished.”
Source
1863
A.D.
1796–1863
“The fall of the angels is referred to in several passages of the New Testa- ment, although its history is nowhere given. By their revolt they forfeited their places in the empyreal mansions, and incurred a sentence of condemnation. Darkness and chains are symbols of their punishment, which at the end of time will be confirmed in the general judgment to be passed on all intelligent creatures of God.”
Source
1871
A.D.
1871
“(Pe2 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 Gen 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" (Gen 6:2) of the Sethites, than of angels, who, as "spirits," do not seem capable of carnal connection. The parallel, Pe2 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 Gen 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.”
Source

Undated

date unknown
date
unknown
c. 300 B.C.
“And it came to pass when the children of men had multiplied that in those days were born unto them beautiful and comely daughters. And the angels, the children of the heaven, saw and lusted after them, and said to one another: 'Come, let us choose us wives from among the children of men and beget us children.' And Semjaza, who was their leader, said unto them: 'I fear ye will not indeed agree to do this deed, and I alone shall have to pay the penalty of a great sin.' And they all answered him and said: 'Let us all swear an oath, and all bind ourselves by mutual imprecations not to abandon this plan but to do this thing.' Then sware they all together and bound themselves by mutual imprecations upon it. And they were in all two hundred; who descended in the days of Jared on the summit of Mount Hermon, and they called it Mount Hermon, because they had sworn and bound themselves by mutual imprecations upon it. And these are the names of their leaders: Samlazaz, their leader, Araklba, Rameel, Kokablel, Tamlel, Ramlel, Danel, Ezeqeel, Baraqijal, Asael, Armaros, Batarel, Ananel, Zaqiel, Samsapeel, Satarel, Turel, Jomjael, Sariel. These are their chiefs of tens. And all the others together with them took unto themselves wives, and each chose for himself one, and they began to go in unto them and to defile themselves with them, and they taught them charms and enchantments, and the cutting of roots, and made them acquainted with plants. And they became pregnant, and they bare great giants, whose height was three thousand ells: Who consumed all the acquisitions of men. And when men could no longer sustain them, the giants turned against them and devoured mankind. And they began to sin against birds, and beasts, and reptiles, and fish, and to devour one another's flesh, and drink the blood. Then the earth laid accusation against the lawless ones. And Azazel taught men to make swords, and knives, and shields, and breastplates, and made known to them the metals of the earth and the art of working them, and bracelets, and ornaments, and the use of antimony, and the beautifying of the eyelids, and all kinds of costly stones, and all colouring tinctures. And there arose much godlessness, and they committed fornication, and they were led astray, and became corrupt in all their ways. Semjaza taught enchantments, and root-cuttings, 'Armaros the resolving of enchantments, Baraqijal (taught) astrology, Kokabel the constellations, Ezeqeel the knowledge of the clouds, Araqiel the signs of the earth, Shamsiel the signs of the sun, and Sariel the course of the moon. And as men perished, they cried, and their cry went up to heaven...”
Source
date
unknown
Glossa Ordinaria Medieval
“But the angels. And truly those are not to be imitated who falsely say that Jesus is not true God, but a man begotten of both sexes. For if he did not spare the angels who sinned, neither will he spare men who grow proud. They did not keep their own principality. So too men, who do not keep the principality by which through the grace of adoption they were made sons of God. But they abandon their dwelling, that is, the unity of the Church in which they were reborn, or the seats of the heavenly kingdom which they were to receive if they kept the faith; and he will condemn them gravely before the judgment, and more gravely in the universal judgment. With eternal chains. That is, with pride and an impenitent heart. Or the divine sentence which will confine them forever Or the chain is the desire of the lowest things, bound by which they cannot return to higher things.”
Source
Modern · 1953 →

The in-app commentary runs from the Fathers to the early-modern record, then stops — that's where the public-domain sources end, not where the reading does. For the modern reading, follow the sources directly.