encrypt files with different encryption key

David's Avatar


21 Feb, 2012 10:43 AM


I have a huge .pdf 385 MB which I would ilke to encrypt. If I use the services option I can encrypt the whole file. That much I understand. Can I encrypt that file with a different encryption key (or in reality different password to myself?) without using my "standard key"?

Am I on the right track if I add a different user? Or can I add a sub user? I have to admit other then generating the key and uploading my public key a couple of years ago (with which I already had difficulty) I have not mucked around in the gpg keychain application.



  1. Support Staff 1 Posted by Steve on 21 Feb, 2012 06:21 PM

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    Not sure what exactly you are aiming at. You can create as many keys for as many mail-addresses as you wish with GPG Keychain Access. Also you can create a key-pair with a phantasy mail address like [email blocked]. Does that answer your question?

  2. 2 Posted by david on 21 Feb, 2012 07:23 PM

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    Thanks for getting back to me. I guess so... My idea was instead of having to make an encrypted disk image just to encrypt the file with GPG tools. But since it would be just to me and I wanted to use a different password...

    Ahh, in reality it was a half baked idea to start out with but I like your idea of just having a fantasy email address for this purpose.



  3. 3 Posted by david on 21 Feb, 2012 07:45 PM

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    So I created a document encryption user and have a suggestion, which you probably already considered. When GPG2 comes with the passphrase pop up it blocks the paste function.
    I use a password manager, also to generate password but without being able to copy them in I have to reduce length and complexity. With more and more users who are serious about security (us or why would we be here ;-) ) I wonder if it wouldn't be good idea to allow pasting in the passphrase form.

    Just a thought,

    David aka Philly

  4. Support Staff 4 Posted by Steve on 21 Feb, 2012 10:21 PM

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    Hey David :) aka Philly,

    let me do a rough guess: Your password manager is called 1Password? At least that's the most used around.

    I use that myself (not the dropbox though, I don't think that it's smart to sync your passwords over US-servers). We already sent the company behind 1Password a feature request and they said, that it would be possible but currently too low of a priority to make it into the software.

    Please send them a request. The more this feature is demanded the sooner we will see it. I'd love to have that functionality too.

    Good night,

  5. 5 Posted by david on 22 Feb, 2012 09:33 AM

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    Hi Steve,

    Of course 1Password ;-) , as for the dropbox and us issue... I go back and forth on that. I REALLY like the functionality and read 1Password's white paper... Their encryption seems pretty solid and would need to first be broken. I don't doubt the US can do that BUT they could probably also hack our computers (all Chinese and US) anywhere in the world.... But in principle I agree with your stance....

    For that reason I have bought myself a NAS and will try to move more data out of their cloud and onto my private one... But then again I like the icloud feature set (and that data is pretty scary).

    Then again I was surprised when I read the bad internet policies the German government implemented a couple of years ago and even the Swiss who usually are pretty good about privacy force ISPs to keep a record of every email to and from plus IP address's associated with those eMails plus the subject title which pass through their systems...

    Soo, we have to go to extremes to protect our privacy ;-(

    Ah well, sent the functionality request. I was a little confused though. I can copy it from 1Password but it blocks the paste function in the GPG program (at least is says something in the top left (can't remember maybe GNU ?) and blocks the passte function there... I'll try to take a screen shot next time.


  6. Support Staff 6 Posted by Steve on 24 Feb, 2012 10:01 AM

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    hehe, since you know what I think about dropbox you'll most likely be able to transfere that to iCloud. But many people use it and I respect that decision.

    The so called "Vorratsdatenspeicherung" is a difficult topic. It just arrived in autria a few days ago. And I was astonished that the protest doesn't seem to be huge.

    Protecting privacy can become a full time job if you take it seriously. So it's always a trade off. Or you get a typewriter and only send via snail mail and even then you are not entirely safe.

    About copy & paste: I'm 100% positive that this is fixed in the code. So on our side there's no obstacle. But 1password needs to support pinentry. I'm not sure though if it is already in the public code. But will be once we release GPGMail stable version (sometime (hopefully) soon(?)). :)

    Cheers, steve

  7. 7 Posted by cfraire on 29 Feb, 2012 02:16 AM

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    Steve, please would you elaborate on what one would need to put in a request to agilebits about 1Password. I'll send it right away once you let me know.

  8. Support Staff 8 Posted by Luke Le on 29 Feb, 2012 04:57 AM

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    Hi cfraire,

    unfortunately due to the nature of the gpg-agent, there's probably no integration with 1Password possible.
    But at least it should be possible to copy & paste into the password field.

  9. Support Staff 9 Posted by Steve on 29 Feb, 2012 04:41 PM

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    Hi all,
    this is possible. It should be possible to use the default 1P keyboard shortcut, but AgileBits needs to do some enhancements to pinentry to make that work. Please tell them that we'd be happy to assist with any questions that might arise.

    @cfaire You can reach AgileBits on various ways (Twitter, User Forum, Tener Support platform, ...). Choose one :)

    All the best, steve

  10. Luke Le closed this discussion on 14 Mar, 2012 11:57 PM.

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