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ErikKohler's avatar
ErikKohler
Copper Contributor
May 29, 2024

Outlook S/MIME issue - encryption makes mail unreadable

Hello all,

 

since a few weeks some coworkers including myself expierence a strange behaviour in Outlook. All Outlook clients are set up to encrypt every mail via S/MIME. Some external contacts can't read those encrypted mails, that's why we deactivate the encryption for those mails over die encryption button in Outlook. If we then send the mail out, the mail appears as encrypted in the "sent mails" folder, the recipient can't open the mail and the sender itself can't even open it. It seems like Outlook has some major issues with the S/MIME encryption. 

Has anyone experienced any similar behaviour or maybe has a an idea what could cause this problem?

 

Cheers,

Erik

  • JeffL327's avatar
    JeffL327
    Copper Contributor
    I have a user that is seeing a similar issue that just started appearing in the past 2 weeks.
    We have a sensitivity label that is setup to Encrypt Only if the applied to a sent email.
    Once the email is available in her sent items folder, it is only accessible for a few minutes.
    After that, the encrypted email cannot no longer be opened.
    Has anyone else experienced something similar or found a workaround/resolution?

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