It is possible to manually toggle sign for a message, I wonder how it can be done for any message created?


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.


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).

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