Routing mail through exchange 2016

Dear Experts,

I have a single exchange server 2016 standard server in a 2012R2 domain with about 20 mailboxes.  I have been tasked with installing a Sophos Mail encryption product (SPX) so that selected messages can be encrypted.  The SPX is a virtual appliance and it has been setup and configured.  

So in order to have the encryption work, outgoing messages must be routed through the SPX.  The appliance will pickup on the keywords and apply the encryption as necessary.  Some senders were getting NDRs but I believe this was due the SPX not having an FQDN configured (separate issue - I'll get that sorted I'm sure).

Now I have been asked to deploy Exclaimer to add disclaimer notes to the end of messages. So I'm wondering how I can route mail properly.  I'm guessing:

mail client  >  exchange connectors  >  SPX

I'd thought of:
mail client  >  exchange connectors  >  SPX  >  another exchange connector

but that looks a bit silly.

Who is Participating?
IvanConnect With a Mentor System EngineerCommented:

Usually when you implement something like that, you reconfigure Exchange to route mail thru it.
So I guess you should reconfigure send connector, and in delivery tab, change to "Route mail through smart hosts" and enter ip address of SPX. That would route email from Exchange to SPX, and then SPX would route to internet.

Client --> Exchange --> SPX --> Internet

Viral RathodConsultantCommented:
No need to change anything.

Please create transport rule which will add disclaimer to your outgoing mails.

Following article will help you to create transport rule for disclaimer.
Tom CieslikConnect With a Mentor IT EngineerCommented:
Ivan has right, but also You need to put your SPX IP in your External DNS as A record and add it to you SPF record to be legit for recipients server.
To generate SPF you can use simple internet SPF generator.
Making Bulk Changes to Active Directory

Watch this video to see how easy it is to make mass changes to Active Directory from an external text file without using complicated scripts.

Annie RoseTech LeadCommented:
Outbound Mail Flow for Exchange Server 2016:

Learn about mail flow and the transport pipeline in Exchange 2016:

Exchange 2016 - Mail Routing:
Ajit SinghCommented:
Is there any update?
tech53Author Commented:
Thanks folks. I struggled with this for a while.  I created a FQDN for the SPX and corresponding SPF record.  No problems since.
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