Any free PGP solution for Outlook 2010? (Win 7)

Discussion in 'privacy technology' started by pajenn, Jul 1, 2013.

  1. pajenn

    pajenn Registered Member

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    I use Thuderbird with Enigmail for personal email, but I need Microsoft Outlook for some work things, and many of my email contacts use it, so I'm wondering if there's a PGP plugin for it (preferably free) similar to Enigmail?

    I'm aware of gpg4usb, which is a great tool for occasional, portable use, but too inconvenient for regular use with Outlook emails.
     
  2. happyyarou666

    happyyarou666 Registered Member

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    im wonderin here what exactly it is that thunderbird is lacking here, it does have addons you do know that right ;)
     
  3. pajenn

    pajenn Registered Member

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    the problem is that i cannot force my employer or email contacts to use Thunderbird instead of Outlook. convincing certain email contacts to install a PGP plugin for Outlook might be do-able though, if one exists.
     
  4. PaulyDefran

    PaulyDefran Registered Member

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    Use GPG4Win and install GPGShell 3.78.

    -http://www.jumaros.de/rsoft/index.html-

    You can use the "Current Window" option to encrypt anything. You could also use GPG4USB, but it would be a little more involved (copy and pasting).

    PD
     
  5. Creer

    Creer Registered Member

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    In latest Beta version 2.2.0 of Gpg4win, - GpgOL starts supporting Outlook 2010.
    Full changelog: http://lists.wald.intevation.org/pipermail/gpg4win-announce/2013-July/000055.html
     
  6. Escalader

    Escalader Registered Member

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    Hi Creer:


    Rather than mess with all the various email clients, Outlook, Thunderbird that others have why not just encrypt the message as an attachment?
    I mean how many secret messages do we send per year?

    OR are the goals here different and I just have missed the point again?:doubt:
     
  7. pajenn

    pajenn Registered Member

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    well, I'd like to encrypt all my messages, not just the "secret" ones because I don't like other people reading my email. of course it's hard to get other people on board, which is why the encryption scheme should be convenient.

    by the way, I did try GPG Shell, but I get the following error message: "This version of GPGshell requires at least GnuPG v1.4.10 or later. / Your version (v1.4.9) does not fulfill this requirement, please update." However, I do have the the latest version of Gpg4win installed, but I think I also have an older version as part of some other package (MinGW), which some other software required, so I'm not sure what to do about this.
     
  8. Creer

    Creer Registered Member

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    Hi Escalader,

    do you mean to compress .txt file with message with password?
    If yes then this method needs at least one truely secure channel which will be used to give other person (recipient) the password to unzipp message.
    GPG eliminates this - you can send messages over insecure channels - you don't need to give password to decrypt message/file to recipient.

    Also note that using GPG/PGP you can also sign messages/files and other person can verify then two things:
    - the author of message
    - integrity check of the message (to be sure nobody [MITM] modify the message)

    About secrets aspect:
    http://www.lugod.org/presentations/pgp/why.html

    Quote from this post: https://www.wilderssecurity.com/showpost.php?p=2241600&postcount=92
     
    Last edited: Jul 16, 2013
  9. Creer

    Creer Registered Member

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    Have you tried latest beta which I mentioned few post above?
     
  10. pajenn

    pajenn Registered Member

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    just installed it. needs a reboot. will report back later.
     
  11. pajenn

    pajenn Registered Member

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    update on my try of gpg4win-2.2.0-beta31:

    installed fine, added GpgOL (or something) tab to outlook 2010 (32-bit version). i then sent myself an encrypted message (from a different account) and pressed decrypt, entered password and boom, outlook crashed. next time i started outlook the GpgOL tab was gone. i re-ran the gpg4win-2.2.0-beta31.exe installer, but the GpgOL tab didn't come back, and I don't want to spend a lot of time jerking around with this, so that'll be my testing. from the little i saw it looked promising, but i think enigmail for thinderbird is better than this GpgOL for outlook at the moment, or maybe just more mature (enigmail has more features, easier to use, prompts for password to decrypt message automatically, etc.)

    i did the test on a virtual machine with 32-bit version of outlook (which I hadn't updated with MS updates, so that could be the problem), anyway... i won't try this again until they have a final release out because it would be mainly for other people and I don't want to subject them to beta software. also, i wonder if it works with 64-bit version of outlook...
     
  12. Creer

    Creer Registered Member

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    Sorry to hear that. It's the problem with beta - on some machines it works on the other don't.
    I don't use Outlook as mail client (I use Claws Mail with GPG plugins) so I haven't tested it but I believe your feedback about GpgOL would be helpful for Gpg4win team.
     
  13. Escalader

    Escalader Registered Member

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    Yes, I can encrypt the txt, a word message what ever. I can provide my recipients with the tool to read the encrypted attachment and the key code I can provide verbally. Lavasoft's Lavasoft Encrypted File (SFX) is free for them and they don't need to buy Lavasoft to read what I send.
     
  14. Creer

    Creer Registered Member

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    From what you wrote I guess it works similar like having txt or other file compressed with password (AES 256) via free 7-zip.
    And this method has one big disadvantage - password has to be provided to recipient via secure channel. It's up to you (if you are the sender) to check/decide if chosen by you method is really secure - and it probably is if you chose face-to-face method.

    Also I'm not sure if mentioned by you application has ability to not only encrypt and decrypt files but also to sign and verify the author. I cannot find this application to check by myself, there is only paid DigitalLock by Lavasoft on their website.

    BTW. Please note: PGP is commercial (since Symantec bought it) - paid, while GPG is 100% free and supports almost all OS platforms.
    So no matter which your recipient OS is - he/she would be able to decrypt/encrypt/sign/verify message using free GPG.
     
  15. Escalader

    Escalader Registered Member

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    thanks Creer! :D

    We are a bit OT here as I'm talking a paid application for the encrypt and decrypt capability with this DigitalLock. BUT the reader is free. Yes we have to agree the password in a secure way. I could say to my old classmate the surname of the calculus professor all lower case no blanks and you would have it.

    I can sign my document with the creation of the original pdf then encrypt that.

    The latest posts seem to still causing Outlook 2010 issues don't they?

    I like the idea of o/s independent encrypt ability BUT tell me How with the free products I would give you the professors surname?

    Take it easy!!
     
  16. Creer

    Creer Registered Member

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    You are welcome :)
    Right but what if you have to send document as specific extension (not pdf) or send .exe, .bat, or .dll file? (not encrypted but only signed to verify integrity and the author)
    Yes since it's new beta it's normal. However this plugin (installed with Gpg4win) works like should with previous versions of Outlook.
    Also note that you don't have to have Outlook to send encrypted/signed using by GPG mails - you can do that with TB or CM or by other more popular extension for web browser (mailvelope, etc).
    Also you can encrypt/decrypt/sign/verify anything from selected file or from clipboard using cmd or Kleopatra, GPA or WinPT, etc.
    I don't understand this one since I'm not sure what you are trying to say. o_O
     
    Last edited: Jul 18, 2013
  17. Escalader

    Escalader Registered Member

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    That was unclear sorry :cool: Let me try again. Your post was:


    Now I as the user want to send you an encrypted email attachment. The password/key is the name of our favourite teacher so only those who know that fact could decrypt it. How with PGP or GPG do I convey the key to you without compromising the key?
     
  18. Creer

    Creer Registered Member

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    If you are want use PGP/GPG first you have to create pair of keys.
    It means that after this process you will have 2 (two) keys:
    1) your private key
    2) your public key

    Private key should be stored in secure place - you never should send this key to others.
    Public key is a key that should be public - you can send this key to other person even more, you can also upload this key to keyserver where it will be easily to find eg. http://pgp.mit.edu

    The primary benefit of public key cryptography is that it allows people who have no pre-existing security arrangement to exchange messages securely. The need for sender and receiver to share secret keys via some secure channel is eliminated; all communications involve only public keys, and no private key is ever transmitted or shared.

    If you want to encrypt message for me you will have to have:
    - my public key (only I will be able to decrypt message since only I have my secret key)
    and
    - your private key (befor process of encryption start you will have to put your own password declared when you generated pairs of keys at the beginning)

    If you want to sign message for me you will have to have:
    - only your private key (my public key is not needed)

    If I would like to decrypt message from you I will have to have:
    - your public key
    and
    - my private key

    Hope it's more clear now for you, how GPG/PGP works.
     
  19. Escalader

    Escalader Registered Member

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    It is clear now thanks!
     
  20. Creer

    Creer Registered Member

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    You are welcome Escalader :thumb:
     
  21. Creer

    Creer Registered Member

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    Just let you know - stable Gpg4win 2.2 has been released:

    changelog:
    GpgEx now works on Windows 64 bit. Gpg-agent may now be used as Pageant (PuTTY authentication agent) replacement with additional smartcard support. Pinentry now allows to paste in the passphrase. Kleopatra no longer crashes when started by a regular user on terminal servers (Windows Server). GpgOL provides rudimentary support for Outlook 2010 and 2013. Extracting a tarball through the Kleopatra GUI now works reliable Added mkportable.exe as a tool to create a portable installation. Kleopatra now allows it to generate keys with a size up to 4096 bit.
    GnuPG: 2.0.21
    Kleopatra: 2.2.0
    GPA: 0.9.4
    GpgOL: 1.2.0
    GpgEX: 1.0.0
    Claws-Mail: 3.9.1
    Kompendium DE: 3.0.0
    Kompendium EN: 3.0.0

    Download: -http://ftp.gpg4win.org/gpg4win-2.2.0.exe
     
  22. pajenn

    pajenn Registered Member

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    Thanks for the update notice.

    Anyone know if the Outlook plugin (GpgOL) works for 64-bit Office, or is it 32-bit only? Anyone here using this with Outook? (I mainly use Thunderbird, but I have contacts who use Outlook and I'd like to refer them to Gpg4win if it's now stable with Outlook).
     
  23. NipponBill

    NipponBill Registered Member

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    I've only used the Gpg4win 2.2.0 GpgOL on 32-bit Outlook on 64-bit Windows 8. It crashes my Outlook frequently. I had to run several DLLs in Compatibility Mode just to get it to run.

    Alternatively there's an add-on called Outlook Privacy Plugin that isn't as robust feature-wise as GpgOL, but it works without crashing Outlook.
     
  24. pajenn

    pajenn Registered Member

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    Gpg4win 2.2.0 seems to work on my 32-bit Windows 7 with 32-bit MS Office 2010 (although I just used it to send and receive a few encrypted emails for testing), but it did conflict with the AV/FW I had installed on that system until I whitelisted all the relevent Gpg4win files. However, it still doesn't work on my 64-bit Windows 7 with 64-bit MS Office 2010, specifically the GpgOL plugin doesn't show up in Outlook's add-ins options.
     
  25. audia4

    audia4 Registered Member

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    Both gpgOL and OL privacy plugin are free - from my experience that is the only good thing I tell about them. Crashing Outlook, no 64 Bit Outlook support, no HTML,....

    If you really want to work with encryption daily you cannot use them.

    I can recommend http://www.gpg4o.com, which is unfortunately not free, but works really hassle-free.
    Our company uses it in several combinations of Windows and Outlook.
    They also offer a free trial.

    Mark
     
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