Situation: After migrating Micrsoft tenant using Quest-on-demand, the client can’t send email to gmail with this error message:
550 5.7.64 TenantAttribution; Relay Access Denied [ValidationStatus of ‘CN=chicagotech.net’ is CertificateExpired] [AM7EUR03FT021.eop-EUR03.prod.protection.outlook.com 2023-10-05T14:05:40.792Z 08DBC59CBFCC3CE2]
Troubleshooting: When migrating Tenant, the client creates temporary certificates for Quest-on-demand on their DNS record.
chicagotech.net. 60 IN MX 0 bt-esg-uksouth-1-1.odmad.quest-on-demand.com.
chicagotech.net. 60 IN MX 0 bt-esg-uksouth-1-2.odmad.quest-on-demand.com.
We find the quest on demand server is on the relay outbound by going to Exhange admin center under Mail flow Connectors,
The resolution is disabling BT-IntegrationPro-Out… in Rules whch fixes the problem.