How does one attain (or fail to attain) the grace of God in this context? Is this speaking of initial salvation or something else?
ESV - 15 See to it that no one fails to obtain the grace of God; that no "root of bitterness" springs up and causes trouble, and by it many become defiled.
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Although Paul is not specifically named or credited as the author of Hebrews, I think that the idea being expressed here is similar to a subject that he is known to have spoken of in his epistles (such as to the Galatians (as in Galatians 3:1-5)) and the Ephesians (as in Ephesians 2:8-9)) of not trying to mix salvation by grace through faith with salvation by works. Any attempt on the part of people to make salvation dependent in any way, or to any extent, on human works and conduct -- or to teach others to do so -- is futile, and (as the writer of Hebrews noted) will fail, and will make salvation by grace alone through faith alone impossible and of no effect. Yes, people who have been saved are to conform their conduct to God's standards in gratitude to Him for the salvation that they have already received. But that conduct is not what saves them. It is an effect -- not a cause.
The KJV, in this particular text, is a more insightful translation from the original Greek and reads like this: “Looking diligently lest any man fail of the grace of God; lest any root of bitterness springing up trouble you, and thereby many be defiled (Heb 12:15 KJV). A word by word analysis of the text will reveal the following: Looking diligently: being constantly on guard Lest any man fail of the grace of God: Lest anyone should fall from the grace (gift) of God. Lest any root of bitterness springing up - A root of bitterness signifies a poisonous plant - Hebrews refer to every poisonous plant as bitter (wormwood) - Proverbs 5:4; Jeremiah 9:15; Lamentations 3:15. The root of bitterness is used here metaphorically for a bad man, or a man holding unsound doctrines (akin to idolatry), spreading false doctrines in the Church - see Deuteronomy 29:18. Trouble you: disturbs you (just as the poisonous plant would), with false doctrines and bad example. And thereby many be defiled: One bad example in the Church can corrupt or contaminate many others, and by this destroying many in the Church.
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