1) From what I understand, I can imagine that you are looking for a way to route specific emails to Exchange Online and other mail to Exchange on-prem. If this is the case you can make the use of mail policies on ESA and SMTP routes where you can configure what traffic is routed where. E.g. all traffic for domain example.com goes to Exchange Online and traffic to example2.com goes to Exchange on-prem. Now if you want to send emails for specific email ids to a different destination other than configured for in the SMTP route then I would recommend creating a new incoming policy/filter for those specific recipients and apply set action of "alternate-host" for emails to be delivered to a separate destination.
2) I would recommend you to create a new private outbound listener for Office 365 and added the partial host ".protection.outlook.com" in the RELAYLIST. Also, recommended you to remove all the IP Addresses of exchange from the incoming listener's RELAYLIST and add all of them into the Outbound 's RELAYLIST, so outgoing listener can be used specifically for the outgoing emails.
3) From O365 if you send an email internally, it should not go through ESA and that email routing needs to be done in O365 otherwise it might cause a loop. If you are routing the emails through ESA, then email will be processed through the same SMTP routing and keep looping and this can be configured in O365.
Cisco is happy to announce their Fall release, FTD 6.7/ASA 9.15.1/FXOS 2.9, which consists of 104 features across 24 initiatives, addressing technical debt while staying true to our five core investment areas: Ease of Use and Deployment, Unified Policy an...
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