On 10 Jul 2016, at 9:12, y...@gmx.de wrote:

Hi there,

I have two IMAP accounts where the business account should use encryption by default and a second private account which should not encryption. My settings are as in the
attached screenshot.

By default (opening a new composer window) encryption is enabled and my private email from my business account is selected. For sending a private email I have to my private identity and the encryption option remains on...so I always have to uncheck the encryption option which is kind of annoying...is there any reasonable way for having the encryption/signing options per account and not based on some vague "history" magic? It's just not working as expected.

I just want to add whatever reinforcement to this plea I can. I won't even try to explain the full complex of failure modes I've run into with the history-based system, but I've got more addresses than I can count and multiple PGP keys and S/MIME certificates, so it mostly does not work. Since keys & certs are bound to *sending* addresses, it makes no sense to make sign/encrypt guesses based on the recipient addresses.

Use cases that break:

1. Mailing lists. I mostly use list-specific addresses which mostly DO NOT have any key I can sign messages with. Those addresses are aliases for an account that has both a PGP key and a S/MIME cert. Some people sign their messages to mailing lists, so if I reply, MM wants to sign my reply but it has no key it can use for that.

2. In my primary professional role, I may use any of 3 distinct accounts with entirely different addresses that I use in different circumstances for business-political reasons too silly and mundane to explain. While the set of recipients does play a role in which address I want to use and whether I want to sign or encrypt a message, the complete decision for what account to use and what sort of crypto treatment to apply is immune to deterministic digital logic. I don't even get it right all the time, since another input is "who might this be forwarded to?" and I never cease to be amazed by that.

3. Talking to myself. Occasionally I have reasons to send myself mail from one account to another, in encrypted form. Every time I try this, MM does something that causes the GPG passphrase dialog to come up asking for the passphrase *of the recipient's private key* which is definitely not right.

I think the first thing to fix is to bind the sign/encrypt and protocol choices to the From address tightly and never try to second-guess the user's sending address choice at sending time. I THINK that's what is happening in (3) and I've had too many wrong-sender events not involving crypto to accept them all as user error. If there's no way to sign or encrypt a message from an explicitly chosen or MM-selected address, don't try to do so automatically and don't offer those options. Also, do not open up the sender choice to robotic change at sending time, no matter how strange the sender/recipient pairing may seem to the logic in MM.
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