I'm getting the same issue. background: I am automating a base deployment with ansible. The architecture consists of 3 clustered indexers, 3 clustered search heads, 1 cluster master, 1 deployment server, 1 license master. I was able to login without ssl configured. I then edited the web.conf file to enable web ssl and pointed it at the private key and server certificate. I then wiped the servers and re-ran the ansible scripts. I also have splunk running through systemd. I have set the permissions of /opt/splunk to :splunk and made the necessary additions to sudoers. Result: The web UI shows up at the set url registering a valid ssl certificate; however, once I utilize the user to login it fails with a 500 Internal Server Error logs: The web_service.log has the following entry: "File "/opt/splunk/lib/python2.7/site-packages/splunk/rest/init.py", line 500, in simpleRequest raise splunk.SplunkdConnectionException, 'Error connecting to %s: %s' % (path, str(e)) SplunkdConnectionException: Splunkd Daemon is not responding: ("Error connecting to /services/authentication/users/: (')ssl.c:725: The handshake operation timed out',)",)" ... View more