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Say I generate a passphrase with bitcoin core to a wallet.dat, but also have a copy of it before the passphrase generation. Will EVERY address I'll generate AFTER the passphrase will NOT be accessible to the old copy (Before the passphrase) or is it a matter of luck – some addresses will be generated with the old keys and some with the new?

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Will EVERY address I'll generate AFTER the passphrase will NOT be accessible to the old copy (Before the passphrase)

Correct. When encrypting a wallet, every key/address used from that point on will be new and encrypted. The wallet will not delete the old keys of course, otherwise it would lose all the funds before encryption. But from that point on, it will never give you an address from before encryption. There is no luck involved, beyond the usual negligible address collision probability.

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