Exchange 2013 to Exchange 2019 migration

Copper Contributor

Old Exchange 2013 and new Exchange 2019 will be at different sites, connected via a site to site VPN tunnel.

Once I install the initial Exchange 2019 I'm assuming all email will still flow out of the Exchange 2013. Even after migrating all mailboxes to the new server email will still flow out the old Exchange 2013. A few questions -

What is the function of switching to the Exchange 2019 to be the sender and receiver of email? I guess once I add the new delivery IP to my inbound spam filter provider it will start to receive, but what about outbound?
Also, question on SSL certs. We are currently using a single name cert and using an SRV record for autodiscover. It works, but I want to pick up a SAN SSL cert for autodiscover, etc. Is it ok to use a completely new SAN SSL certificate on the new Exchange server? What issues, if any could arise?


Thanks in advance for reading and responding!

3 Replies
I have used this one with a migration of 2013 to 2019, very complete guide:

Do you know you can directly migrate to 2019 from any Exchange Server version?

Here is how:

To change the server that sends outbound, you first need to make sure the new servers are allowed by your network configuration to send SMTP traffic externally, then you update your send connectors so that the new servers are the only ones configured as sending servers.
By default Exchange servers will accept SMTP traffic, so as long as your network points to the new servers, once you configure your spam filter to point to the new server you should be good.
A new SSL certificate can be used on the new servers as long as the certificate is assigned to SMTP and IIS (and POP/IMAP if you are using them) and the correct names are used in the subject or SAN