Batch sending s/mime encrypted email – How

batchemailencryptionmime

I need to send some sensitive data periodically to a set of recipients via email. Due to the nature of the data, we need to send it encrypted.

Some of our clients use PGP/GPG, so it's not an issue, but we have a few cases where the client is not allowed/does not want to use PGP, as they're already using S/MIME internally.

Is there a way to script/automate the process of encrypting and sending the email in those cases? Any tips/tricks?

For the moment, as they're not too many cases, we're solving it by emailing the PGP file to one of us and manually "converting" it to S/MIME email (basically, open PGP email, forward, send), but we'd like to do it in a "cleaner" way.

Thanks a lot

Javier

Best Answer

Try:

$ openssl smime -sign -in cleartextmail.txt -signer my_cert.pem -text \
| openssl smime -encrypt \
-from you@example.com -to someone@example.org \
-subject "Signed and Encrypted message" \
-des3 user.pem | sendmail someone@example.org

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Security – Easiest way to send encrypted email

We've had to go through something similar with our clients for PCI. The best way would be to use some version of PGP/GPG.

Now that being said, it really isn't as painful as you think. We have done this with hundreds of non technical users. What we did was choose two products - the free GPG (which Kronick states have GUI front-ends) as well as the pay for PGP software. We wrote up some really good documentation that could be sent to our clients instructing them how to use the software that they chose as well as trained our Account Managers on basic troubleshooting and how to use the software.

That has kept 95% of the issues that clients run into out of the IT queue. For the other 5% we made IT resources available to answer questions, as well as in the worst case get on a call to help the client out.

As an alternative we also bought some licenses of winzip so that we could use the built in AES encryption with a pass phrase. The commercial PGP software has the ability to create an encrypted file that is opened by passphrase only as well. Although honestly using PGP has worked out so well i think i only create these types of files 2 or 3 times a year.

Delivery status notification, invalid header: bad MIME

There must be an empty line between the message or MIME headers and the message content:

------=_NextPart_b45f3c386576f1955bb5338634f5047f_alt
Content-Type: text/plain; charset="utf-8"
Content-Transfer-Encoding: 8bit
Return ID: 1
Return Date: 11/09/2011

Here you'll need an empty line between Content-Transfer-Encoding: 8bit and Return ID: 1.

If Return ID and Return Date should be headers, they are syntactically wrong. Headers must not contain a whitespace in the header name. Valid headers would be Return-Id and Return-Date.

Best Answer

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Delivery status notification, invalid header: bad MIME

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