I solved my problem.

I remote debugged my application running on Server 2008. After stepping through some QT code, I noticed an SSL handshake error.

I ended up creating a custom NetworkAccessManager where I overrode the createRequest method.

Inside the createRequest method, I grabbed the sslConfiguration object from the request object and called setPeerVerifyMode(QSslSocket::VerifyNone).
Qt Code: 
  1. QNetworkReply * myNetworkAccessManager ::createRequest (Operation op, const QNetworkRequest& req, QIODevice* outgoingData)
  2. {
  3. 	QSslConfiguration config = req.sslConfiguration();
  4. 	config.setPeerVerifyMode(QSslSocket::VerifyNone);
  5. 	config.setProtocol(QSsl::TlsV1);
  6.  
  7. 	QNetworkRequest request(req);
  8. 	request.setSslConfiguration(config);
  9.  
  10. 	return QNetworkAccessManager::createRequest(op, request, outgoingData);
  11. }
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Perhaps someone knows why the SSL is failing to handshake on my Server 2008 box but not my Windows 7?