Troubleshooting MMA Agent Configuration with SSL Proxy

Problem description

You might encounter this error message during the setup wizard of the Microsoft Monitoring Agent.

Moreover, the MonitoringAgent.log file might contain a similar message

Rejecting certificate since it did not chain to a trusted 
root, actual root was CN=XXXX, OU=XXXX, O=XXXX 2018-03-06T15:45:21.1858236-06:00 

Debug: Failed to trust remote certificate: The underlying connection was 
closed: Could not establish trust relationship for the SSL/TLS secure channel. 

Possible cause

This is likely caused by the presence in the network of a device (aka intercepting proxy) that perform HTTP inspection on web traffic.

For additional information: HTTPS Inspection and your PKI


In order to resolve, bypass HTTP inspection on the device for the following URLs

Resource Port number Bypass HTTP Inspection
* 443 Yes
* 443 Yes
* 443 Yes
* 443 Yes

As described as a requirement for Azure Log Analytics in the following article

Connect Operations Manager to Log Analytics - System requirements

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