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Hey Eric, this unfortunately is expected behavior. What you are experiencing is a bug in ESXi. More information is available in the Install/Admin Guide under the Troubleshooting Log Insight section or at the following KB article: http://kb.vmware.com/kb/2003127.
ESXi Logs Stop Arriving in Log Insight
After restarting the Log Insight service, syslog messages from ESXi hosts stop arriving in Log Insight.
Problem
Configuration changes in Log Insight require that you restart the Log Insight service. After the restart, syslog feeds from ESXi are no longer available.
Cause
Certain versions of ESXi stop sending logs if the connectivity to the remote syslog listener is interrupted, even briefly. This problem affects the following ESXi versions, depending on the communication protocol that is used.