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I'm not sure I could really comment on which one is 'safer'. That is, if they both are using 256 AES, then the theoretical security is equal, the only differences in security would be things like how well they protect their memory spaces from being swapped, etc. However, I would go with gpg, because it's really meant for this kind of thing. That is, openssl is really the solution for encrypting streams (http connects, ssh, etc) and gpg is a solution for block encryption (files, things of fixed length).
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