Might be a windows issue:
https://social.technet.microsoft.com/Forums/windowsserver/en-US
/44b0ee8f-bb22-4e1c-8de0-21578d204cfc/win-2k8-ldap-with-ssl-anfd-gssapi-
kerberos?forum=winservergen

I'm still updating this server, will try again after the update is
finished.

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https://bugs.launchpad.net/bugs/1576799

Title:
  Regression: 2:4.3.8+dfsg-0ubuntu0.14.04.2 Failed to Issue the StartTLS
  instruction

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