I just had the first problem (Kubuntu 10.10). I believe I followed
outdated instructions on the web. I then followed

http://wiki.aptosid.de/index.php/Verschlüsselung_in_kmail_einrichten

(sorry, German only) and then pinentry-qt4 worked as expected. Only
after reading the tutorial I understood that in an up-to-date KDE4
system, the gpg-agent is automatically started if it is enabled in
~/.gnupg/gpg.conf or ~/.gnupg/options at login time. I also changed the
content of ~/.gnupg/gpg-agent.conf to

# ~/.gnupg/gpg-agent.conf
pinentry-program /usr/bin/pinentry-qt4
no-grab
default-cache-ttl 86400
max-cache-ttl 86400

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https://bugs.launchpad.net/bugs/371178

Title:
  pinentry-qt4 doesn't prompt for a password when trying to read an
  encrypted email in Kmail

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