Microsoft Outlook: Emails encrypted with S/MIME cannot be opened. The error message "Internal error." appears.

Assume the following scenario:

  • A user receives an e-mail message encrypted with Secure/Multipurpose Internet Mail Extensions (S/MIME).
  • The message cannot be opened.
  • When opening the message, the following error message is displayed:
Leider besteht ein Problem beim Öffnen dieses Elements. Dies kann vorübergehend sein. Wenn dieser Fehler erneut auftritt, sollten Sie Outlook neu starten. Fehler im zugrunde liegenden Sicherheitssystem. Interner Fehler.

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Microsoft Outlook: Find out recipient certificates for S/MIME encrypted mails

For troubleshooting e-mail messages encrypted using Secure/Multipurpose Internet Mail Extensions (S/MIME), the encrypted part of a message can be exported. See article "Microsoft Outlook: Extracting an encrypted S/MIME message from an email ".

To find out with which certificates a message has been encrypted, you can proceed as follows...

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Microsoft Outlook: Extracting an encrypted S/MIME message from an email

The encrypted part of an e-mail message encrypted with Secure/Multipurpose Internet Mail Extensions (S/MIME) is always contained in a file called "smime.p7m" as an attachment to the mail.

Outlook does not display this attachment, but for analysis purposes it can be extracted from the e-mail with MFCMAPI , which Microsoft provides free of charge.

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Microsoft Outlook: View which algorithm was used for an S/MIME encrypted or signed email

Below is a description of where it is possible to view which symmetric algorithm was used to encrypt an email received, and which hash algorithm was used for a signed email.

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