Yes - Tridion will check you every time. In other words, every time you make a web request, a new TDSE or session will be created. It can be much more often than you think. I donβt know the details for SDL Tridion 2011, but in R5 days I remember that it took 6 authentications to load the initial GUI view.
It is very likely that authentication on an LDAP server can be cached. The old ISAPI filter did this, but I donβt remember how authorization requests are cached. There has never been a strong requirement to support exotic or "heavy" LDAP integrations.
Previously, there was a setting that would make the TDSE GUI cache, but it was only an experimental function of internal use. I would not recommend using it, and it is very clear that this configuration is not supported.
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