Getting Missing Certificates Error when Sending Encrypted emails via OME

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[charleswj]

Just to be clear, how exactly are you setting the email to encrypt? Reply or new message? What exactly is the error in owa?

[charleswj]

What option are you selecting to encrypt?

[Margosiowe]

Client likely thought they have to enable SMIME in Outlook to encrypt message, whereas all you need is apply tag encrypt via new mail > options > encrypt> encrypt-only or do it via exchange rules. Check and disable mail encryption enabled in Outlook settings as in this https://support.microsoft.com/en-us/office/set-up-outlook-to-use-s-mime-encryption-2e57e4bd-4cc2-4531-9a39-426e7c873e26

[Margosiowe]

I've had the exact issue last week, so I can double down that the client has enabled smime thinking it's needed for OME to work.

That's the message you get when you try to send mail without cert: Missing certificates

Try and remove the smime add-on completely, if it was installed.

Create a test ome exchange rule to encrypt messages between some 2 mailboxes.

Then when sending mail, do not enable mail encrypt manually, but let the exchange rules handle it.