Could be something as simple as the timeout on the initial ping expiring.
Are the response times getting closer and closer to 2 seconds (or whatever
your timeout is) as the packets get bigger? VPN can add significant
processing overhead at each end, so a 1 or 2 second timeout may not be enough.
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http://www.groupstudy.com/form/read.php?f=7&i=9432&t=9363
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