Feature request: per sender signing/encryption options

barry's Avatar


09 Jul, 2017 06:38 PM

I just started using GPGTools, and I have to say that it solves one of my biggest complaints with Apple Mail. Thanks! I'm using 2.7b3 on macOS 10.12.5 and so far, it's working great.

I'm coming from Claws Mail on Ubuntu, and there are just a couple of things I've noticed. This discussion is for a feature request that CM has which is quite nice. I'd like to be able to enable/disable automatic signing and encryption per sender (From) address. The reason is that I use one address to email friends and family and I don't want to sign those messages. I use other addresses for free software discussions and I want to always sign those.

I know that I can manually set the flag per composing email, but it would be really nice to have defaults that generally pick the right option.

  1. Support Staff 1 Posted by Steve on 10 Jul, 2017 04:00 PM

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    Hi Barry,

    we have a ticket to allow users to define encrypt by default and sign by default on recipient basis. I think that would cover your use-case. I connected this discussion with the existing ticket. That means, should this discussion get closed, it will be re-opened as soon as the ticket is closed. That way you'll stay in the loop and get notified as soon as we have news. Feel free to open a new discussions should you run into further problems or need assistance.

    All the best,

  2. 2 Posted by barry on 10 Jul, 2017 07:57 PM

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    Hi Steve, thanks for the reply. Just to be clear though, I'm looking for
    per-sender signing/encryption rules, not per-recipient.

    What's the use case? I have a dozen or so email addresses defined, some are
    personal, some are work related, and others are for my open source work. I
    generally do not want to sign/encrypt emails from my personal addresses since
    that'll just confuse my family members :). I *always* want to sign (and
    occasionally encrypt) emails from my open source addresses, and usually from
    my work addresses.

    Because I interact on so many open source forums, it would be a hardship to
    specify per-recipient signing rules (e.g. I join a new mailing list or email a
    new contributor, I don't want to have to whitelist them for signing

    I should also note that even if the default is to sign or not, there should be
    an option/button to override on any specific email message I'm composing.


  3. Support Staff 3 Posted by Steve on 10 Jul, 2017 08:05 PM

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    If you use [email blocked] for all personal communication and you say you do not want to sign/encrypt email, am I correct to assume you do not have a key for that email address?

    If so, those emails will will not be signed.

    Same for [email blocked] → create a key for that and enable sign / encrypt by default.

    Would that not cover what you are asking for?

  4. 4 Posted by barry on 10 Jul, 2017 08:21 PM

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    Hi Steve,

    Actually, yes I still have a key for [email blocked], and *occasionally* want to sign messages from the personal addresses, but not by default.

  5. Support Staff 5 Posted by Steve on 10 Jul, 2017 08:25 PM

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    Sounds like a legit use-case. We'll discuss in team and probably create a new ticket for this feature request.

  6. 6 Posted by barry on 10 Jul, 2017 08:30 PM

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  7. Support Staff 7 Posted by Steve on 10 Jul, 2017 08:40 PM

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    Btw, not sure if you where responsible for those fixes but thanks for making mailman handle PGP/MIME signed messages (without breaking them) :)

  8. 8 Posted by barry on 10 Jul, 2017 09:08 PM

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    It’s a group effort, but thanks! Now you know another reason why I love your project. :)

  9. Support Staff 9 Posted by Steve on 11 Jul, 2017 03:02 PM

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    We have an existing ticket for "Smart" detection of security method, sign/encrypt status based on email history.

    I think that would actually fit your use case. So instead of creating an additional similar feature request I linked that existing ticket to this discussion. What it will be in the end if unclear. Defaults per account is likely easier to implement and smart detection should cover many more use cases.

    Let me know if you agree that would cover your case.

  10. 10 Posted by barry on 11 Jul, 2017 03:23 PM

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    Hi Steve, yes that sounds interesting for sure. I’d have to play with it to see how it fits with my workflow, but if the history detection is good, it could in practice cover the use case nicely.

    For example, I have 30 years of email and hundreds of folders. Mail.app used to be painfully impossible to archive messages properly because it required scrolling through pages of folders (and Mail.app still doesn’t support proper folder subscriptions). But newer Mail.app seems to autodetect the folder to archive a message to based on previous history and in practice it works really nicely, greatly improving usability.

    Thanks again!

  11. Support Staff 11 Posted by Steve on 11 Jul, 2017 03:27 PM

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    Yeah, Mail.app has a ton of bugs. We've filed quite a few which have not been fixed for some years now.

    Note that this feature is not on the near term road map. As you probably can image we are still working on finalizing GPGMail for 10.12 so a stable can be released. And next up on the horizon is macOS 10.13. So those are the current priorities.

    I'm closing this discussion. Should you need further assistance or have questions you can re-open this discussion here or open a new one any time.

    Kind regards and thanks again for your input,

  12. Steve closed this discussion on 11 Jul, 2017 03:27 PM.

  13. barry re-opened this discussion on 11 Jul, 2017 03:35 PM

  14. 12 Posted by barry on 11 Jul, 2017 03:35 PM

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    No worries Steve, I understand how it goes!

    It does kind of shock me how much Apple neglects Mail.app.

  15. Support Staff 13 Posted by Steve on 11 Jul, 2017 03:38 PM

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    Couldn't agree more.

  16. Steve closed this discussion on 11 Jul, 2017 03:38 PM.

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