On Thu, 26 Jan 2012, Who Me wrote:
I suspect that I have either mis-configured exporting my SSL cert from my Exchange 2010 server, mis-configured something when extracting the pem for use in squid or fat-fingered my squid config some how. Yet - the thing that is making me crazy is that all of this works for OWA. So if I did any of the above, why would OWA work and not Active Sync?
Something you might consider just as a troubleshooting tool is using stunnel + your cert to set up a SSL server on a different port redirecting to Squid's non-SSL listening port. Comparing results might give you some clue where the problem lies.
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