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GNU Privacy Guard automation of file encryption?

I was tasked to automate an encryption of a data extraction output. It's basically a query to a SQL table and saved as a .csv file. Then I want to be able to use GNU Privacy Guard and encrypt the file.

Is there anyway to automate this process? I was maybe SSIS and then use xp_sendmail (Transact-SQL)
to send the email with the file attached.
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Rich Rumble
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What sort of information, is it subject to any additional laws or regulations like FISMA(gov't), PCI(creditcard/SSN), HIPAA(patient/doctor)? Is Public key cryptography required or will password protection do? GPG/PGP can be complex to setup and maintain the keys and their exchanges, especially with non-tech savvy folk. We like to use AES-256 bit encryption from 7zip and maintain an offline list of passwords (printed to paper as opposed to keeping on a PC).
-rich
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btan

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