I can confirm the bug with kde4.2.1 as provided by "deb
http://ppa.launchpad.net/kubuntu-experimental/ubuntu intrepid main" in
/etc/apt/sources.list. I reacently upgraded for 8.04 to 8.10.

There are at least theses 2 bug reports, which seem to be related: 
https://bugs.launchpad.net/bugs/262748
https://bugs.launchpad.net/bugs/268951

Temporary workaround (see link in comment 3 and 4):
End kmail (or whatever is supposed to ask for the passphrase) and from a 
console: 
$ eval "$(gpg-agent --daemon)"
$ kmail

Permanent Workaround (untested):
Put "$(gpg-agent --daemon)" into /.kde/env/gpgagent.sh

In my humble opinion, all the bug reports, including this one, are
assigned to the wrong packages (kdepim, gnupg, enigmail). As nobody with
another desktop environment than KDE seems to have a problem (??), some
KDE-package (kdebase* or kdelibs*) might be more appropriate.

As the issue seems to be unsolved for more than 3 months and the bug
renders the system unusable for sending signed and reading encrypted
mails for a 'normal' user, being a regression from 8.04, one might
consider to change the importance of the bug.

Some system information:
gnupg                                      1.4.9-3ubuntu1
gnupg-agent                                2.0.9-3.1
gnupg2                                     2.0.9-3.1
gpgsm                                      2.0.9-3.1
gpgv                                       1.4.9-3ubuntu1
kdebase-bin                                4:4.2.1-0ubuntu1~intrepid2
kdebase-data                               4:4.2.1-0ubuntu1~intrepid2
kdelibs-bin                                4:4.2.1a-0ubuntu1~intrepid1
kdelibs5                                   4:4.2.1a-0ubuntu1~intrepid1
kdepimlibs5                                4:4.2.1-0ubuntu1~intrepid1
pinentry-qt                                0.7.5-2ubuntu1
pinentry-qt4                               0.7.3+svn799201-1ubuntu1
# update-alternatives --display pinentry
 link currently points to /usr/bin/pinentry-qt4
$ im-switch -l
Your input method setup under en_GB locale as below.
=======================================================
No private "~/.xinput.d/en_GB or ~/.xinput.d/all_ALL" is defined.
=======================================================
The system wide default is pointed by "/etc/alternatives/xinput-all_ALL" .

-- 
kmail: cannot sign emails after upgradind to intrepid ibex
https://bugs.launchpad.net/bugs/297976
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