Error solved
This problem was solved with the Outlook plugin version 1.9.7265.10954 (published on 22.11.2019). You can download the latest Outlook plugin here.

Initial situation: When trying to send an encrypted email from Outlook, the following error message appears: Checksum mismatch at 0 of 20.

Solution: The following steps are necessary as a workaround until an updated version of the add-in fixes this error:

  1. Delete the REDDCRYPT accounts in the REDDCRYPT Addin settings
  2. Close Outlook
  3. Delete the accounts.json file, which you can find under %appdata% for Windows\Common
  4. Start Outlook and add the existing account in the REDDCRYPT Addin again
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