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As the Israelites did not trust God's conduct, God ruled none of them would enter the promised land. Only their children would. (Deut. 1: 34-36) Deut. 2: 14-16 confirms the outcome.

From Deut. 5 on, Moses sums up the events from the exodus until then, recapitulates the law and renews the covenant. Doing this, he repeatedly adresses the people as if they have been eyewitnesses (Deut. 5: 5 etc.). Consider Deut. 29: 2-3:

2 Moses summoned all the Israelites and said to them: Your eyes have seen all that the Lord did in Egypt to Pharaoh, to all his officials and to all his land. 3 With your own eyes you saw those great trials, those signs and great wonders.

How does that go together? Until when has the first generation died?

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Keep in mind that the decree that they will die before entering the holy land only included those twenty years and older,

In this wilderness your bodies will fall—every one of you twenty years old or more who was counted in the census and who has grumbled against me.

And this age is repeated many times throughout the OT.

Thus a lot of the adults and teens (13-20) that witnessed the Lord's miraculous deeds in Egypt with their own eyes were indeed standing there as Moses addressed them on that day.

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  • It is also important to remember that not all the people had rebelled. Joshua, Caleb, Eleazer, and Ithamar were probably middle-aged men when they left Egypt and all of them went into Canaan.
    – oldhermit
    Sep 11 '21 at 12:35
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Deuteronomy 29:

2 Moses summoned all the Israelites and said to them: Your eyes have seen all that the LORD did in Egypt to Pharaoh, to all his officials and to all his land.

Gill explains:

which many now present had seen, and were then old enough to take notice of, and could remember, though their fathers then in being were now dead:

Benson adds more:

Some of them had seen, when they were young, the plagues which God had brought upon Pharaoh and his people, in order to accomplish their deliverance; and others from them had understood these things, which is often termed seeing, both in the Scriptures and elsewhere.

In an indirect sense, all of them 'saw' (understood) those great trials, those signs and great wonders.

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