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I'm having the exact same problem trying to send via TLS to a mailprovider. We can send without problems to their testserver that uses a self-signed certificate. To their production server with an official certificate it fails. I checked that our keystore has their valid root and intermediates.
We're about to start sniffing on the network to catch the handshake but perhaps you have something to share?
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Hans
Feedback response number WEBB8XUCWJ created by ~Tate Desnuskiakol on 09/05/2012