#1483 new
Volker Kopetzky

S/MIME encryption mangles special characters

Reported by Volker Kopetzky | June 8th, 2016 @ 09:36 AM

When sending an email with special characters like german umlauts (äÄöÖüÜß), the receipient see's them as encoded strings, e.g.
können shows as k=C3=B6nnen.

It worked before (as oh so often), and I used another computer where I downloaded the key/certificate again. Yet it now happens on all machines.
I tried exporting/importing the certificate and private key to the osx keychain, but the problem persists.

My main issue right now is that I do not have a working instance where the umlauts can be read.

Any other ideas?

Comments and changes to this ticket

  • Volker Kopetzky

    Volker Kopetzky June 8th, 2016 @ 11:22 AM

    Seems to be fixed now, I'll try to document this for the internet eternal.

    1. Generate usual S/MIME stuff
      • private key
      • certificate (cert-A)
      • e.g. startssl
    2. Import to os x key chain
    3. exchange signatures with addressee
    4. Send emails with nice umlauts
    5. Setup a scond computer (and forget to copy your certificates)
    6. regenerate certificate with the same key
      cert-B has the same signature as cert-A but different hashes/fingerprint and expiration date than the initial one
    7. send email with cert-B
    8. receiver gets scrambled umlauts
    9. ask receiver to import your new cert/signature again
    10. receiver sees nice umlauts again

    Sender: MailMate/mac
    Receiver: Outlook/Win

    Kinda makes no sense, does it?

  • benny

    benny June 13th, 2016 @ 07:43 AM

    • State changed from “new” to “cantreproduce”

    What you see as mangling is the so-called quoted-printable encoding. This is used to convert message content to 7 bit (for historic reasons). The problem is unlikely to be related to keys/certificates. It is more likely to be some kind of issue (sender or recipient) which makes decoding the message fail.

    If you get MailMate back into this state (in that case, try sending a message to me via “Help ▸ Send Feedback” such that I can see the issue myself).

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Mac OS X email client.

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