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How to encrypt sent mail?

2018-07-10
2018-07-14
  • Chiabuotu Sazonova

    I want to store mails that I send encrypted, regardless whether they were sent in an encrypted way or not.

    I've set up a filter whete the only criterion is that the folder is "Sent", and the action is encrypting to a certain key (defined as 0x...). All boxes are checked as to when the filter should be performed.

    Am I doing that the right way?

    I'm quite unsure because in my mail client, I can open and read these sent mails after clearing my passphrase and even after restarting my client and not entering the PGP password. Everything else that is supposed to be encrypted is unreadable as it should be, but these are not. However, if I go to my mail provider's online interface, there these same mails look like PGP-encrypted mails, unreadable. How is that possible?

     

    Last edit: Chiabuotu Sazonova 2018-07-11
    • Patrick Brunschwig

      It depends on what you want to achieve. If you want messages to be encrypted after sending, then it does not matter where the message is stored, but when the filter is triggered: after sending.

      If you what to encrypt already sent messages, then you need to run your filter on the folder, otherwise nothing will happen (menu Tools, Run filters on Folder).

       
  • Chiabuotu Sazonova

    I want to achieve the former (automated encryption of a mail after it's sent and stored in my Sent folder).

    My emphasis is not which folder it's stored in, but rather what criterion to define in the filter. If it's indeed irrelevant what criterion I give, and what matter is only that "After sending" is checked, then what criterion should I give to the filter?

    My current filter, as defined above, already makes the mail server store the encrypted version, but for some reason Thunderbird still stores an unencrypted version of the mail.

     
    • Patrick Brunschwig

      You can fill in anything that matches every sent mail.

      For example: "From" "Contains" "@"

       
      • Chiabuotu Sazonova

        I extensively test-drove this function and here's what I found.

        I can use both "From" "Contains" "@," and/or "Folder" "Is/Contains" "Sent", it will encrypt the mail after Sending and I see the encrypted version on the server. This is all good. However, locally, it sometimes saves the encrypted version, and sometimes the decrypted version. I manage to get the encrypted version less often that the decrypted one, and it works or doesn't periodically.

        Also, in sent mails which get encrypted, after I decrypt and view them in the Sent folder, the characters with diacritics are substituted with "�" or with an uppercase letter unrelated to the original one. I use UTF-8 for my mail. The recipient sees proper rendering, it looks garbled only on my end.

        From these I infer that encrypting sent mail introduces some situations which are uncharted for the software.

         

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