> Date: Thu, 15 Nov 2018 11:17:58 +0100
> From: Christian Heusel <christ...@heusel.eu>
> To: Enigmail user discussion list <enigmail-users@enigmail.net>
> Subject: [Enigmail] Recipient causes the bcc mails to be encrypted
> Message-ID: <fc4c8d5f-d40a-79c2-8c84-99a15a3a5...@heusel.eu>
> Content-Type: text/plain; charset="utf-8"
>
> Dear Enigmail developers,
>
> before I start to describe my problem / unexpected behavior I want to
> say thanks to all of you for maintaining this awesome plugin. :D
>
> The problem I am facing is the following: I want to send an Email to a
> larger group of people most of them in Bcc as I dont want the addresses
> to be public,
> one of the recipients has GPG Keys and turns on the autoencryption from
> gpg. That causes all the people in BCC not being able to read the mail.
>
> Is this behavior intended?
>
> Best wishes from Germany
> Chris
>
> Version: Enigmail version 2.0.8 (20180804-1515)
> Thunderbird: Thunderbird 60.3.0
> OS: Arch Linux
>
Your post to the Enigmail list intrigued me.  I tried an experiment or
two to try to duplicate your issue.

First I composed an email to two users, putting both of their addresses
in the TO: field.  Note that I had a PGP key for one user, but no key
for the other.  I selected "Encryption ON" on the Composition Toolbar. 
Enigmail refused to send the email, complaining about the lack of a key
for the one user without a key.

I repeated the experiment using BCC: for both users.  The email was not
sent due to the missing key.

I put the user with no key in the BCC: field and the user ID with a key
in the TO: field.  Nothing, due to the missing key.

I put the user with a key in the BCC: field and the user with no key in 
the TO: field.  Enigmail refused to send it due to the missing key.

The I repeated my experiments using Per-Recipient Rules.  I defined
rules for the two users.  No matter what I tried, I could not get
Enigmail to send the email - encrypted to one but not encrypted to the
other.  I chose Encrypt for the user with the key and no encryption for
the user for whom I had no key.  Nothing.

In my opinion, this SHOULD work ...but it does not appear to be
possible.  The last time I use PGP (now called Symantec Encryption
Desktop), it was possible to send an email to several people each with
different encryption and signing settings.  For example, if I sent an
email to three people using PGP, I might specify the following settings:
Encrypt-PGP/MIME and Sign for User-One, Encrypt-PGP Partitioned and no
signature for User-Two, and no encryption and no signature for
User-Three.  In the background, this would result in three SMTP
sessions, each sent to a different SMTP RCPT TO address. (See RFC
5321.)  In effect, the email is sent three times.  The requested
encryption and signing settings are applied to each email according to
the previously chosen selections.  Of course, any address in a BCC:
field would not be listed in the To: field of the RFC 822 header.

Chris, I know that I haven't really solved your dilemma.  Sorry. 
Enigmail engineers, got any thoughts?  I'd like to be able to do what
Chris is trying to do too.



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