[Gpg4win-users-en] Totally insane - gpg4win GPGol won't encrypt or sign!

Bernhard Reiter bernhard at intevation.de
Mon Sep 14 13:06:17 CEST 2009

Am Sonntag, 13. September 2009 10:56:20 schrieb Bo Berglund:
> In order to get a firm ground to check the workings of gpg4win
> I again uninstalled everything I had previously installed concerning GPG.
> Then I also rebooted my XP-Pro PC and tried to erase the GnuPG directory
> in preparation for a new install.

dependency hell can hit you on windows as well and it is possible
to get broken installations by many means. (Often without involving Gpg4win at 
all). To be really, really clean you possibly would need to reinstall 
windows. :( For Gpg4win it is good to try to use the regular de-installation 
for each version before you are installing a new one.

> First problem:
> --------------
> Windows would *not* let me erase the directory because there was
> a dll active out of this dir (pcre.dll)!
> I have no idea which process on my PC could have loaded this dll
> since all GPG related stuff was uninstalled and I had not started
> any program yet (except for Windows Explorer).

No idea either, maybe something like the dependency viewer can help you to 
find the application that loaded it.

> So I figured I would install gpg4win 1.4.1 anyway since it probably
> wants to use this dll too...

1.1.4 ..

> After installation I am now able to use GPGee from the Windows Explorer
> context menu to decrypt and encrypt files on my disk. This was not
> possible before the uninstall/install cycle.
> Next problems:
> -------------
> But now Outlook 2003 is even more weird in its ways....
> 1) If I write a message and set it to be encrypted (plaintext of course)
> then GPGol (I assume) shows a dialog box when I click the Send button.
> In this dialog box I am requested to select the keys to be used for
> encryption. So I do this and continue.
> ==> The outgoing message is sent *without* encryption in clear text!
> 2) If I again make a test message (plain text) and set it to be signed
> then GPGol shows a dialog asking me for the signing key and passphrase.
> Then it sends the message *unsigned*!

Uh, no idea again. Please try 2.0.rc1 if you do not use Exchange.

> Enigmail test
> =============
> Since I have Enigmail installed on this computer as well (I use
> Thunderbird for one of my mail accounts) I made two test messages in TB
> where I signed one and encrypted one.
> ==> BOTH of these were properly handled!!!

Well it is much easier to integrate crypto in another Free Software
like Thunderbird where someone has the source code.
(See my other post about technical GpgOL difficulties.)

> So the end result is that it looks like there is something broken
> with GPGol and I am now at wits end as to how I can debug this problem.>
> All help welcome!

Personally I would try 2.0.1rc1 and if the issue persists,
try to enable debugging output, 
see 23.2 in (German, but you'll get it)

> I really need this GPG to be integrated in Outlook 2003 since
> this is where all of my normal mail is handled and I cannot easily change
> since I have many many many thousands of archived messages in Outlook that
> I need access to.

You will have a backup as a sane IT-person, which is good.
If you were okay with a different product like TB, Claws or Kontact, which is 
Free Software, personally I would recommend you look into migrating your 
email archive to a non-proprietary format. As far as I know there are several 
methods to migration .pst files from Outlook.


Managing Director - Owner: www.intevation.net       (Free Software Company)
Germany Coordinator: fsfeurope.org. Coordinator: www.Kolab-Konsortium.com.
Intevation GmbH, Osnabrück, DE; Amtsgericht Osnabrück, HRB 18998
Geschäftsführer Frank Koormann, Bernhard Reiter, Dr. Jan-Oliver Wagner
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