As a gtk+/gtk-2 program claws-mail/smime-plugin should depend on gnupg/pinentry with gtk use-flag enabled, because without that flag claws-mail crashes (no passhprase popup will appear) and will only work if you start it from command line, because pinentry asks for the key there. Reproducible: Always Steps to Reproduce: 1.USE="-gtk" 2.install claws-mail and claws-mail-smime
Fixed in CVS