Hebrews 2:2 For since the message declared by angels proved to be reliable, and every transgression or disobedience received a just retribution, 3 how shall we escape if we neglect such a great salvation? It was declared at first by the Lord, and it was attested to us by those who heard, 4 while God also bore witness by signs and wonders and various miracles and by gifts of the Holy Spirit distributed according to his will.
Your description of the timing is not correct. When we see the 'sign of the red dragon' that is the last woe and correlates to the third thing that 'Israel' will encounter when they are tempted to go into spiritual Egypt.
Isaiah 30: 1 “Ah, stubborn children,” declares the Lord, “who carry out a plan, but not mine, and who make an alliance, but not of my Spirit, that they may add sin to sin; 2 who set out to go down to Egypt, without asking for my direction, to take refuge in the protection of Pharaoh and to seek shelter in the shadow of Egypt! 3 Therefore shall the protection of Pharaoh turn to your shame, and the shelter in the shadow of Egypt to your humiliation. 4 For though his officials are at Zoan and his envoys reach Hanes, 5 everyone comes to shame through a people that cannot profit them, that brings neither help nor profit, but shame and disgrace.”
6 An oracle on the beasts of the Negeb. Through a land of trouble and anguish, from where come the lioness and the lion, the adder and the flying fiery serpent, they carry their riches on the backs of donkeys, and their treasures on the humps of camels, to a people that cannot profit them. 7 Egypt’s help is worthless and empty; therefore I have called her “Rahab who sits still.” 8 And now, go, write it before them on a tablet and inscribe it in a book, that it may be for the time to come as a witness forever.
Isaiah 31:1 Woe to those who go down to Egypt for help and rely on horses, who trust in chariots because they are many and in horsemen because they are very strong, but do not look to the Holy One of Israel or consult the Lord!
Revelation 8:13 Then I looked, and I heard an eagle crying with a loud voice as it flew directly overhead, “Woe, woe, woe to those who dwell on the earth, at the blasts of the other trumpets that the three angels are about to blow!”
This ‘witness’ is a sign to Israel that records the ‘travel’ of ‘Israel’ into spiritual Egypt. The Negeb is in southern Judea whereby one would travel to get to Egypt. A portion of ‘Israel’ is trying to ‘return to Egypt’, the place that God had rescued them from. The ‘oracle’/ prophecy is that on this journey to Egypt they would encounter:
- 1) lions,
- 2) adders, and
- 3) the ‘flying fiery serpent’.
We see this spiritually in each of the
three woes (the 5th, 6th & 7th Trumpet, respectively).
Thus, ‘Israel’ has a temptation to go to spiritual Egypt, back into spiritual slavery. In Isaiah 30:6 above we saw the lion, adder (snake), and flying fiery serpent.
In Revelation, we see that
- the locusts of the 5th Trumpet (1st woe) have ‘lion’s teeth’ (Rev 9:8),
- the horses of the 6th Trumpet (2nd woe) have ‘tails like serpents with heads’ (Rev 9:19),
- and at the 7th Trumpet (3rd woe) we see the ‘flying fiery serpent’ = the ‘sign of the red dragon in heaven’ (Rev 12:3). The Greek here for ‘red dragon’ would be ‘pyrros drakon’. ‘Drakon’ meaning ‘dragon’ which means a ‘serpent’. ‘Pyrros’ means ‘fire-like’ or ‘fiery red’.
- Rev 11:8 mentions spiritual Egypt that is tempting them
When Isaiah says that the ‘fiery serpent’ is ‘flying’, it is ‘in the sky’. The Greek word for ‘heaven’ (‘ourano’) can either mean spiritual heaven or the skies above. So when Revelation 12:3 says, ‘a great red dragon appeared in the sky’ as a ‘sign’, we can directly point to Isaiah’s ‘flying fiery serpent’ as a reference that is a ‘witness forever’ (Isa 30:8) as a sign in heaven (Heb 2:4).
Rev 9:7 In appearance the locusts were like horses prepared for battle: on their heads were what looked like crowns of gold; their faces were like human faces, 8 their hair like women’s hair, and their teeth like lions’ teeth; 9 they had breastplates like breastplates of iron, and the noise of their wings was like the noise of many chariots with horses rushing into battle.
Rev 9:18 By these three plagues a third of mankind was killed, by the fire and smoke and sulfur coming out of their mouths. 19 For the power of the horses is in their mouths and in their tails, for their tails are like serpents with heads, and by means of them they wound.
Rev 12:3 And another sign appeared in heaven: behold, a great red dragon, with seven heads and ten horns, and on his heads seven diadems. 4 His tail swept down a third of the stars of heaven and cast them to the earth. And the dragon stood before the woman who was about to give birth, so that when she bore her child he might devour it.
The 'fiery flying serpent' is related to the idea of the 'seraphim' which literally means in Hebrew 'fiery serpent' and is also a type of angel from Isaiah 6:2.