Topic: Microsoft Outlook had problems encrypting this message

When I send an email with S/MIME encryption the error pops up, "Microsoft Outlook had problems encrypting this message". Why does Outlook give me this pop up every time?

Re: Microsoft Outlook had problems encrypting this message

That seems to suggest that Outlook cannot connect to a remote server. If that's the case and the network connection genuinely hasn't been lost then it may be that a repair/reinstall is the easiest option as determining the source of erroneous errors like this can be rather time-consuming. If that doesn;t work then I'm afraid I have no better suggestions.
For more information:Outlook recovery