[Gpg4win-users-en] GPGol fails to sign/encrypt outgoing messages!

[Bo Berglund]

> -----Original Message-----
> From: IW [mailto:iain at holuwon.com] 
> Sent: Sunday, September 13, 2009 2:15 AM
> To: gpg4win-users-en at wald.intevation.org
> Cc: bo.berglund at telia.com
> Subject: Re: [Gpg4win-users-en] GPGol fails to sign/encrypt 
> outgoing messages!
> 
> -----BEGIN PGP SIGNED MESSAGE-----
> Hash: SHA1
> 
> Pada Sat, 12 Sep 2009 17:24:25 +0200, "Bo Berglund"
> <bo.berglund at telia.com> menulis email dengan judul ([Gpg4win-users-en]
> GPGol fails to sign/encrypt outgoing messages!):
> 
> > I have a hard time understanding how this encryption/signing system
> > works...
> > 
> > Today I have encountered the same pronblem *twice*:
> > 
> > 1A) I sent a message to a recipient from whom I have received his
> > public key in order to verify his ability to decrypt the message. So
> > I typed my message, then clicked the "Encrypt" button in Outlook and
> > then adjusted some text and finally sent the message.
> > ==> It was *NOT* encrypted!!!
> > 
> > 1B) I opened the sent message and found that it was 
> unencrypted, so I
> > used the function in outlook to resend the message and this time I
> > clicked the button *immediately* before clicking the send button.
> > ==> This time it was encrypted
> 
> If you type a message and then sign/encrypt it and then edit again
> ity will of course invalidate the signature/encryption. It may be
> that on MO if click encrypt/sign the programme assumes you want to
> sign/encrypt at that point. So do not edit further. The fact that this
> occurs every time you edit post click button suggests I am correct.
> ANyhow, it is a good habit to learn - do not edit after you decide to
> sign/encrypt.
> 
> If true a bit silly but then M$ and MO are not the best out there.
> 
> IW
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> Version: GnuPG v1.4.9 (GNU/Linux)
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> iEYEARECAAYFAkqsOaAACgkQ90Gf33Iu52VrngCgrEcEcxvkFsdrlt+H+dEZhiyn
> bdgAoMtcM5pfkCzo2taMXZXltmpcoVR4
> =pAjM
> -----END PGP SIGNATURE-----
> 

However, even if I do not touch the message after activating the Sign
function but go directly to Send it won't sign the damned message!
In *both* cases it briought up the dialog for me to enter my passphrase
and select the key to sign with, though. And this happens at the time
I click the Send button both directly and after I have added some
more text.

I do not believe GPGol signs the message at the time the Sign button
is clicked, that just sets a flag. The real signing is part of the
sending procedure as witnessed by it displaying the keyselect and
passphrase dialog only after clicking Send.

There must be something else going on.

Just a minute ago I found another peculiarity:
I wanted to encrypt a file as an example for my co-workers so in
Windows Explorer I rightclicked the file and selected the pop-up
menu item "GPGee/Encrypt(PK)" command.
At this time I expected to get a dialog asking for the keys to
use for encryption but exactly *nothing* happened!

What does this mean? Is that not the way to encrypt standalone
files?

--
Bo Berglund