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Try the suggestions at this site: David Gardiner - Dave's Daydreams: Windows 8 Mail and Exchange using a self-signed certificate While he was trying to get Windows 8 Mail to talk to an Exchange server with a self-signed certificate, the same should apply to Outlook on Windows 8.

I ran into this same problem and finally figured it out. I had to download the dovecot.pem and exim4.crt files from my personal email server manually (via sftp) and then import them into Microsoft's certificate store as valid root authorities, since they are self-signed certificates. Once I did...