Redirect the message to the following connector

Question

We need to create a pilot to test the EOP mail work-flow starting with same users only.
In O365 it is possible creating a new connector and use a rule to redirect those selected users to this connector.

Unfortunately in my case this is not possible as we have as first point an on-prem server that should redirect the mails to O365.

The mail-flow is: on-prem server1>> O365 EOP stand alone (Anti-spam) >> on-prem server2

The option "Redirect the message to the following connector" is not present on an on-prem server clarified also at this post:
https://learn.microsoft.com/en-us/answers/questions/311426/missing-condition-for-mailflow-rule-in-exchange-20.html

In this scenario what could be the best way to test the mailflow starting with few users?

Answer 1

Are you in hybrid mode? The connectors should have been created automatically.

If your users are on-prem and you want to send out mail through EOP for only those users, that is not possible for on-prem unless you use a third party solution:

https://jaapwesselius.com/2018/04/19/source-based-routing-in-exchange/
https://www.emailarchitect.net/easbr/kb/exchange_server_sender_based_routing.aspx
https://www.ivasoft.com/routebysender2013.shtml

Answer 2

At the moment on the on-prem server1 is present a send connector that point to a local 3rt part Antispam (that need to be replaced). The idea is create a second send connector where re-redirecte only few users to test the EOP Antispam.

Do you think is possible?

Answer 3

we are not in hybrid mode with the server1 but we are in hybrid mode with the server2 (EOP , that is stand alone).
In reality the problem is not to create a connector but to test the flow (from server1 to O365) only with a small group of selected users. To test the functionality of the EOP we would like to separate 10-15 users from the ordinary mail flow to re-direct them to O365. In this way we could use 2 connectors the main one that provide the main mail service to the current antispam (3rd party) and the second that points to O365 to test the EOP with few users. The scope here is to have a pilot environment to test the behaviour of the initial setting of the EOP using few users instead to move all users mail traffic directly to O365 in once.

Answer 4

Thank you Andy.

I am going to look at the first 2 options.

About ivasoft, do you know if this company is still working? I have tried to contact them (by form and email) in the past but I didn't receive a contact back.