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Transparent mode results in random timeouts. We tried various things trying to find the issue while running in transparent mode, then recently discovered the issue goes away in proxy mode. Not sure if this is a common or known problem with a fix?
See your running V19, I guess I can tick that off as another possibility to try 
First thought it is wan load balancing, tried keeping things like inspection to almost non-existent, switch off authentication from AD etc. but still stuck. Direct proxy so far the best workaround, but it is just that, a workaround that comes with its own caveats.
