I get an internal security error when trying to block or permanently delete these emails with the red badge (icon).


Do you mean this icon?

enter image description here

This icon means the email has a valid digital Signature. (What do the Outlook icons mean?)

For Encrypted emails, try Shift+Delete and choose Yes.

Some ways are also mentioned in these similar threads:

Unable to delete email: "Your digital ID name cannot be found by the underlying security system"

Can't permanently delete an encrypted e-mail...

Since you no longer have the certification to operate the encrypted message, the workaround is to drag these emails to a new PST file and then delete that PST file.

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