In the process of migrating from our current mail system to O365. We will be keeping our MX records on the On Prem Cisco ESA and all messages Inbound/Outbound will go through it. We will be looking to move the ESA to the cloud, but outside the scope of the project.
I'm able to route mail from O365 to our ESA, but the issue that I'm running into to is routing mail to O365 after the migration is complete. I thought that I would just need to modify the "Network > SMTP Routes" and changing the routing to go to O365. Just tested it and did not work.
Is there something else that I need to change? Is the route cached and if so, how do I flush it?
Updating the SMTP routes should be enough for delivery connections to attempt delivery to the O365 server mentioned in the SMTP routes.
You can use the command "delivernow" to reattempt delivery of emails which are queued for delivery on the ESA. Normally the email reattempts delivery as per the bounce profile and the SMTP routes are checked again.
If the emails are not being delivered still you could check connectivity using telnet <O365> 25 and use hoststatus <affected domain> to determine if there are any errors connecting to the the O365 server.
I can confirm that I only have 1 SMTP route. Currently it is set for our current mail server. To test, I changed the entry from current to the route that we have been provided to our O365 tenant.
As a test I changed the SMTP route again to our O365 tenant, restarted the Incoming Mail listener and sent a test email. Email was delivered to our 365 tenant. Changed back to current SMTP route and restart listener, mail flowing back to existing mail server.
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