It is possible to manually toggle sign for a message, I wonder how it can be done for any message created?
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1
Just say
(setq wl-draft-config-alist
'((t (mime-edit-pgp-processing . '(sign)))))
See Section 7.1.4 of the Wanderlust manual, Dynamic Modification of Messages.

jch
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I would simply create my own function that signs and sends, and use that instead.
(I do not use wanderlust and therefore do not know all of its possibilities).

Trevoke
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