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A question was recently asked of me:

Why is Satan Released at the End of the Millennial Reign?

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Why release Satan after the thousand-year
reign of Christ?
Interesting question. Why indeed? Once captured and chained, why not toss him into the lake of fire along with the beast (Antichrist) and the false prophet at the beginning of the thousand years?
There is much speculation, and I must do the same since there is no direct answer provided within the text that addresses this question.
What we know:
Satan is God's great antagonist, destroyer, and accuser of the brethren. He hates God and, therefore, the Jews and Christians more than all of the other humans. He knows that he has been defeated at the cross, yet is uncontrollably compelled to carry out his war against God and try to be "like the Most High." As I understand Scripture, Satan was once the cherub that covered - God's top angel. He had the job of controlling all worship and apparently some oversight of the earth. Then Satan fell and is "sentenced" to the earth along with all of the other fallen angels (although with apparent limited access to the throne room (see Job)). Along comes these humans (Adam and Eve), and
God gives them dominion
over the earth! These puny humans! Not even very
bright. And through subtlety, Satan steals lordship over the earth from Adam (remember when Satan tempted Jesus with "all these kingdom I will give you . . ." (Matthew 4:8-9)? Ever since, there has been a war between good and evil: God and angels and believing saints versus Satan and fallen angels, demons and fallen mankind.
As mankind enters the thousand-year reign of Christ, we know that some 25 percent of the population has survived the Great Tribulation. Many are lost. Some are saved Jews who cried out for their Messiah at the end of the seven-year tribulation period, for example. Assuming a 6.5 billion population today and the tribulation period starts immediately, that would mean that some roughly 1.3 billion people will enter the thousand-year reign in their present day mortal bodies (believers that were raptured prior to the thousand years return with Christ in their immortal, eternal bodies and will no longer pro-create - no marriage in eternity).
We know that at the end of the thousand years, Satan is loosed and stirs up the entire world against the saints, surrounds Jerusalem with a goal of destruction of King Jesus and all his faithful followers, and instead they are wiped out by God with fire from heaven.
What we can infer (speculate):
That a large majority of the 1.3 billion peoples are not saved since the Bible describes the thousand-year reign as a reign ruled with a rod of iron, and that Jesus will deny rain to any nation that does not pay their due taxes. That the nations (and their governments) apparently still exist. The lion may lie down with the lamb, but as far as people go, I suspect that many will only obey because that have to, not because they want to (do I hear murmuring in the desert?).
That these people are mortal, and therefore, can and will have children. Many of these children will also not be saved. I assume that there will still be death, taxes, etc. and that although very different and very just (under King Jesus), people will still be "desperately wicked" (Jeremiah 17:9) except for those who get saved during that time.
That at the appointed times, King Jesus will hold either annual, or otherwise multi-year celebrations or feast at Jerusalem (like a Jubilee - every seventh or fiftieth year), and that believers from around the world attend (both mortal and immortal).
That as one such celebration is taking place, Satan will be released (presumably earlier enough to stir world-wide trouble). It must be a multiple day feast (like the Tabernacle Feast today is seven days), since it would take time to muster the armies of the world to even get there to besiege the city.
Not all of the world can surround the city, even in its enlarged size during the millennial reign. Therefore, the world may be filled with peoples unwilling to fight the King who did not go up to fight - possibly saved mortal folks (very speculative) . . .
What can I conclude:
That Satan in his still seething hate for God will try once more to destroy or disrupt Jesus and His children (saved). Demented, but true.
That Satan is being used by God to test all those mortal folks in the world one last time before eternity begins as to which side they will choose - King Jesus or rebellion.
This is one more test to show mankind that when given a clear choice (remember, during the thousand-year reign, Satan is bound, and therefore, we can assume that pressure to rebel is greatly minimized), man chooses rebellion against God rather than submission to Him. Salvation is by grace. God quickens us, He calls us, not the other way around. Imagine the warped and perverted thinking of those alive, after the thousand-year reign of God's Son to even think about attempting rebellion and insurrection. What hate they must have hidden in their hearts to so quickly go against all they have seen and heard about the King, and try to kill the immortal Son of God and his immortal saints! A Russian pastor touring the United States during Russian Glasnost was asked, "What do you think is/was the most wicked generation?" He replied simply, "The final generation at the end of the millennial reign." He was asked to explain. He answered, "We today see God by faith, not by sight. We preach, believe, and obey His Word. People trust (by faith) what they cannot see with their eyes and must experience by faith. That generation will know Him, see Him, know that He has ruling power, is God's Son, commands the weather, etc. And yet, when stirred up and tempted, after one thousand peaceful years under Christ, they rebel. Not just rebel (as in not paying their taxes), but come to make war with Him and His saints with the intent to kill and destroy Him" (Unknown; paraphrased).
Since Jerusalem is filled with believing saints at the time (presumably during a multi-day feast), I do not believe that God is testing the immortal believers, only the mortal folks in the world.
Why release Satan after the thousand-year reign of Christ? I believe it is to have one last test for all mortals, fallen men to see who they will choose on their own when not quickened by grace through faith - Christ or self.
Maranatha, Church!