I think that’s part of it—SSLSessionCache on the server was set to five minutes.
Dialing it down to 10 seconds seems to have solved the problem
on Safari, but it persists on Chrome, even after a server restart.
It fixes itself after a Chrome restart, so clearly Chrome is doing some caching
of something, somewhere.
What are the consequences of having a low SSLSessionCache value on the server?
Further client diagnosis:
* Chrome 43 OS X renegotiates with the smart card if you open an incognito
window. The same behavior manifests itself in other incognito windows,
though, i.e. if you fail smart card auth it won’t go back and retry
smart card auth. This suggests to me that Chrome is doing some
client side SSLSessionCache, and they maintain different caches
for regular windows and incognito windows, but within each cache
the problem persists.
* Safari 8.0.6 OS X works as expected with the SSLSessionCache setting on the
server side. Dialing up the SSLSessionCache replicates the problem.
So it can be both a client and server side issue.
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