The current sign / encrypt wizard is a bit confusing to use and needs many clicks. User feedback was that it should be simplified. The idea is to move more things into the config. Change the certificate selection and simplify encrypt to self. Also to add signing selection to the recipient selection page. Archiving will be enabled as soon as a directory or more then one file is selected.
A very rough draft:
The Signing certificate selection can be checked. This will enable signing the message and a signature certificate selection. Ditto for encryption.
Encryption certificate selection will be more EMail centric with an autocompleting e-mail line edit and a certificate selection afterwards that looks like the certificate selection dialog used in GpgOL. With a + Button you can add more recipients (or this will be automatic and there will be always a last line.
At the bottom of the dialog there will be some status indication to show what will happen. E.g. If you've selected a mix of OpenPGP / X509 Certificates we want to show that. Also archiving and the general operation should be visible. Not sure yet how to best represent it without using to much space.