
KB No. 2799: CERTIFICATE ERROR FOR ENTITLEMENT.DIAGNOSTICS.OFFICE.COM (WITH OUTLOOK)
Outlook displays a certificate error for entitlement.diagnostics.office.com
Background
Outlook displays a "Security Alert" related to the certificate for entitlement.diagnostics.office.com, indicating that the certificate is issued by olfeo.com.

Procedure
The certificate for the Nginx web server installed on the Olfeo server is displayed because Microsoft's DNS record for entitlement.diagnostics.office.com contains the IP address 0.0.0.0.
| root@machine:/# host entitlement.diagnostics.office.com entitlement.diagnostics.office.com is an alias for ods-entitlement.trafficmanager.net. ods-entitlement.trafficmanager.net is an alias for ods-entitlement-weur-web.cloudapp.net. ods-entitlement-weur-web.cloudapp.net has address0.0.0.0 |
The resolution to 0.0.0.0 causes the proxy to query Nginx, which is listening locally, hence the incorrect certificate. We recommend bypassing the proxy for entitlement.diagnostics.office.com because the expected response will not be received due to the resolution (0.0.0.0). This is likely a request that the workstation must execute locally.