When studying in Hebrews the other night, I was noticing the reference to Psalms 95. Where it states:
"Do not harden your hearts, as at Meribah, as in the day of Massah in the wilderness, when your fathers tested Me, they tried Me though they had seen my work. For forty years I loathed that generation, and said they are a people who err in their heart, and they do not know my ways. Therefore, I swore in my anger, truly they shall not enter into my rest” (Psalms 95:8-11).
Is this stating that they wouldn’t enter Heaven? It would seem so to me. Seems it wouldn’t be Canaan's land since He is speaking in the past tense when He says “Therefore I swore.”
That is what the writer of Hebrews was arguing.
"For He has said somewhere concerning the seventh day: "And God rested on the seventh day from all His works"; and again in this passage, "They shall not enter my rest." Therefore, since it remains for some to enter it, and those who formerly had good news preached to them failed to enter because of disobedience, He again fixes a certain day, "Today," saying through David after so long a time just as has been said before, "Today if you hear His voice, do not harden your hearts." For if Joshua had given them rest, He would not have spoken of another day after that. So there remains a Sabbath rest for the people of God. For the one who has entered His rest has himself also rested from his works, as God did from His. Therefore let us be diligent to enter that rest, so that no one will fall, through following the same example of disobedience" (Hebrews 4:4-11).
David wrote Psalms 95 long after Joshua led Israel into Canaan, therefore the rest was not Canaan but something else (Heaven). It would be granted on a certain day -- "Today" (Judgment Day).
But what God is stating is that those who rebelled were not allowed to enter into the heavenly rest because of their disobedience to Him.
Do you think some of that generation may have repented and made it? Or is this more of a blanket statement that all of those who were over 20 years old when they refused to enter Canaan’s land from their fear. Where at that point judged to wander in the wilderness and die outside of a saved relationship? Essentially only Joshua, Caleb, Moses, and Aaron entering heaven.
Since Moses was among the number who did not enter the promised land, though God indicates he would enter Heaven, we can assume that this was a generalized statement that did not apply to every individual. None but Joshua and Caleb entered the promised land. But we don't know how many of that number would eventually enter heaven, though in all likelihood it would be very few.
Considering all they had seen (Plagues, Red Sea Crossing, Mana, God leading them in the fire and cloud, etc.) it’s hard to imagine why they weren’t happy rather than grumbling and complaining the way they did. They should have recognized they were following their Creator and been humbled.