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Ok I am having a strange issue.
Old Windows 2000 AD server, ssl ldap connect fine.
Ubuntu Webserver, Apache 2.2.17, PHP 5.3.5-1ubuntu7.4
New Windows 2008 AD server, new domain, ldap connect OK, ssl ldap fail
Ok so my webserver is working fine with my old 2k server ldap ssl works great.
I setup my new Win2k8 server and on the server I have no trouble connecting using ldp.exe and ssl, binds with the ldap user account everything.
When I use non-ssl ldap from my ubuntu server it connects great. When I turn on my ssl, it does actually connect according to the log, but right after the ldap_bind the server no longer sends any response. It will just timeout with no response.
I have setup in the adldap script to show any possible errors, but no errors are given, and no response from the server after the ldap_bind. The trace appears to indicate that the php script does continue, but no output. In fact the login works if I hit the server on a different page. Weird I know.
Ok so I even ran an ldapsearch on another Linux server (running identical version of openldap mind) and it works.
When I run the same ldapsearch command on my webserver it gets through everything and then hangs. Apparently this is a very tiny bug in openldap.
I moved that server from openldap 2.4.23 (stable) to 2.4.28 (release) and the problem went away.