SSRS reports not working externally after moving SSRS to a new server

cindyfiller
cindyfiller used Ask the Experts™
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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?
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      Distinguished Expert 2017
      Commented:
      You simply need to authorize the ip of the new server to relay through the exchange server.
      Double check the config on the exchange.
      Presumably the server has a local iis SMTP service configured to send what it gets through the exchange.
      These days as a precaution exchange is usually uses login or authorized IPs to which relay is granted.
      cindyfillerDirector of IT

      Author

      Commented:
      I didn't think I'd need to do that since the other server wasn't listed.  I did add the IP address of the new server to the connector, but I'm still getting the same error.
      Distinguished Expert 2017

      Commented:
      Please clarify?
      On the connector for either port 25, or other, you need to add this ip as authorized to relay.

      Which exchange version are you running make sure you are adding the relay to the correct connector
      cindyfillerDirector of IT

      Author

      Commented:
      Locally we have exchange 2016 - our vendor set it up this way so we could push our active directory out to 365.  Under mail flow / connectors, I have added the public ip of our BI server to the outgoing connector from our internal server to 365.  It is the same spot where Exchange's public IP is listed.
      Distinguished Expert 2017

      Commented:
      You are adding the info on the wrong side.
      Your local Exchange is seemingly the one rejecting, does not allow the new ssrs system from relaying through it.

      The exchange to o365 is likely already has this right.

      Try this,
      From any workstation
      Connect to port 25 of your internal exchange.
      Then when you get a greeting
      Send:
      Ehlo yourworkstationname
      Mail from: <youremailaddress>
      Rcpt to: <external emailaddress>
      See if it is accepted, it you get a relay-denied response.

      Your exchange has to be configured to allow the ssrs ip to relay through it.
      cindyfillerDirector of IT

      Author

      Commented:
      Ok - so I assume I create a send connector...  I've found articles on doing that but it doesn't match the screen when I create a new send connector. Can you provide instructions?
      cindyfillerDirector of IT

      Author

      Commented:
      I found the spot on the server that needed to be changed... all is working now
      Distinguished Expert 2017

      Commented:
      For future, when you get error 5.x.x RELAY DENIED
      this means the system from which the message is being transmitted is not authorized to relay and the remedy is not on the source system but on the destination to authorize relaying.

      Glad you found it, for those who run into the same issue: https://practical365.com/exchange-server/exchange-2016-smtp-relay-connector/

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