CFNetwork SSLHandshake failed (-9806)

Question

When I am trying to configure my Enterprise Mail account(Exchange) in Apple Mail, I can see the following error logs in Console. But I could not see this error while configure same account in Outlook 2011 Mail client. Even I can see the same error logs when I am access my Exchange account via WebMail(OWA).

Is it something specific to CFNetwork API's? I can see the failure error with all the mail clients which using CFNetwork API's for communication.

com.apple.WebKit.Networking[1145] CFNetwork SSLHandshake failed (-9806) com.apple.WebKit.Networking[1145] CFNetwork SSLHandshake failed (-9806) com.apple.WebKit.Networking[1145] CFNetwork SSLHandshake failed (-9806) com.apple.WebKit.Networking[1145] CFNetwork SSLHandshake failed (-9806) Mail[1658] CFNetwork SSLHandshake failed (-9806) Mail[1658] CFNetwork SSLHandshake failed (-9806) Mail[1658] CFNetwork SSLHandshake failed (-9806) Mail[1658] NSURLConnection/CFURLConnection HTTP load failed (kCFStreamErrorDomainSSL, -9806) Mail[1658] CFNetwork SSLHandshake failed (-9806)

Answer 1

Check the certificates your server is using are trusted by the client. I've had the same sort of issue with the Outlook 2016 preview for Mac that we solved by telling OS X to always trust the presented certificate. If you're using a self signed certificate chain like we are then this will probably be your issue.