To reproduce this bug, turn of
"Convenient encryption settings"
and
"Encrypt/sign" replies to encrypted/signed messages"
But don't change the default settings
"Automatically send encrypted = If possible"
and
"To send encrypted, accept = All usable keys"
(or set both settings, if you changed them)
Then reply to an encrypted message from a sender you have a valid public key for. As long as you don't edit the receivers of the message (To or BCC), Enigmail displays
"This message will be unsigned and unencrypted"
Nevertheless, if sending the message it finally gets encrypted. (if you have all necessary and valid public keys)
Looks like Enigmail doesn't checks if it can automatically encrypt when Thunderbird is opening the message composer window and adds the sender of the mail you're replying to. Sadly this behavior is pretty misguiding.
Duplicate to bug 455
Related
Bugs:
#455