I recently moved my Windows 2008 R2 / SQL 2008 R SSRS install to a new server (Windows 2016) and SQL (2014). I thought everything was working fine - we are getting subscriptions emailed internally every day and all of the reports are running fine. However I just discovered that subscriptions to external emails are not being sent out. I'm getting one of two errors:
unable to send to a recipient (happens when I have both an internal email and an external email)
failure sending email – mailbox unavailable with a server response of 5.7.54 unable to relay recipient in a non-accepted domain (happens if it is just external email)
Our exchange server does not have relay/connectors set up for the old SSRS server so I didn't set up relay/connectors for the new one. The SSRS configuration app has the same settings for email on the old and new server. The config file is also identical for email. I'm using the same login to send reports on both servers. I've run a trace on the email from that account and it shows all of the reports sent to internal emails addresses but doesn't show a thing for those sent to external email addresses. I have no clue what is causing the error and don't know if it is because of a difference in Windows versions or SQL versions or ??
Our email is 365 but we have a local exchange server that syncs active directory with 365.
Can anyone help?