I went ahead and added enableSplunkdSSL = false to the server.conf file on both the deployment server and the client. This should remove any issues with SSL. The issue still persists.
Client splunkd.log
08-14-2015 11:34:06.132 -0700 DEBUG DC:PhonehomeThread - PhonehomeThread::main top-of-loop, DC state=Initial
08-14-2015 11:34:06.132 -0700 DEBUG DC:PhonehomeThread - Attempting handshake
08-14-2015 11:34:06.132 -0700 DEBUG DC:DeploymentClient - Sending message to tenantService/handshake
08-14-2015 11:34:06.132 -0700 INFO DC:DeploymentClient - channel=tenantService/handshake Will retry sending handshake message to DS; err=not_connected
08-14-2015 11:34:06.132 -0700 DEBUG DC:PhonehomeThread - Handshake not yet finished; will retry every 12.0sec
08-14-2015 11:34:06.132 -0700 DEBUG DC:PhonehomeThread - Phonehome thread will wait for 12.0sec (1)
08-14-2015 11:34:17.153 -0700 WARN HttpPubSubConnection - HTTP client error in http pubsub Read Timeout uri=http://10.156.101.127:2000/services/broker/connect/0A43BEC6-915B-488E-A60B-8241F1680FAF/IODWAPP242/271043/windows-x64/8089
08-14-2015 11:34:17.153 -0700 WARN HttpPubSubConnection - Unable to parse message from PubSubSvr:
08-14-2015 11:34:17.153 -0700 INFO HttpPubSubConnection - Could not obtain connection, will retry after=71 seconds.
08-14-2015 11:34:18.132 -0700 DEBUG DC:PhonehomeThread - PhonehomeThread::main top-of-loop, DC state=Initial
08-14-2015 11:34:18.132 -0700 DEBUG DC:PhonehomeThread - Attempting handshake
08-14-2015 11:34:18.132 -0700 DEBUG DC:DeploymentClient - Sending message to tenantService/handshake
08-14-2015 11:34:18.132 -0700 INFO DC:DeploymentClient - channel=tenantService/handshake Will retry sending handshake message to DS; err=not_connected
08-14-2015 11:34:18.132 -0700 DEBUG DC:PhonehomeThread - Handshake not yet finished; will retry every 12.0sec
08-14-2015 11:34:18.132 -0700 DEBUG DC:PhonehomeThread - Phonehome thread will wait for 12.0sec (1)
08-14-2015 11:34:30.133 -0700 DEBUG DC:PhonehomeThread - PhonehomeThread::main top-of-loop, DC state=Initial
08-14-2015 11:34:30.133 -0700 DEBUG DC:PhonehomeThread - Attempting handshake
08-14-2015 11:34:30.133 -0700 DEBUG DC:DeploymentClient - Sending message to tenantService/handshake
08-14-2015 11:34:30.133 -0700 INFO DC:DeploymentClient - channel=tenantService/handshake Will retry sending handshake message to DS; err=not_connected
08-14-2015 11:34:30.133 -0700 DEBUG DC:PhonehomeThread - Handshake not yet finished; will retry every 12.0sec
08-14-2015 11:34:30.133 -0700 DEBUG DC:PhonehomeThread - Phonehome thread will wait for 12.0sec (1)
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