Hi Andreas:

Am 07.07.17 12:41 schrieb(en) Andreas Schmidt:
Perhaps an option "encrypt automatically if key is present" could be added to the dialogue in "Manage 
Identities .--> Security" or, more prominent, to "Balsa Preferences --> Mail options (Outgoing) --> 
Other options".

Open “Settings ▶︎ Identities ▶︎ [Identity] ▶︎ Security” and check “remind me if 
messages can be encrypted”.  This will show a dialogue when public keys for all 
recipients are available.  Automatic encryption is not a good idea IMO, as the 
recipient may be in a situation where [s]he has no access to GnuPG (web mailer, 
iToy, Wintendo, ...).

if there are several (encrypting as well as non-encrypting) contacts in the 
To-header?

I don't see the use case:
- Either the message contents shall be kept confidential, then there is no way 
to send it unencrypted even to a single recipient.
- Or you just want to demonstrate that you /could/ encrypt.  Then it is 
sufficient to sign it.

But could sending the same message both encrypted and unencrypted compromise 
keys?

No: 
<https://security.stackexchange.com/questions/42919/can-a-pgp-private-key-be-deduced-if-the-email-text-is-known>.

Hth, Albrecht.

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