Hi @ESJ ,
Welcome to post in our Q&A forum!
I can help you with your questions regarding certificate migration.
Regarding your first question, if you have the pfx file and password used for importing the certificate to the old server, you can use the same to import it to the new server.
As for your second question, when updating your Exchange Server 2016 to 2019, it is not necessary to migrate all self-signed certificates, but it is recommended to do so.
Self-signed certificates are not automatically created during installation. You will need to export and import them manually to the new server.
I have found a similar thread, you can follow this: https://learn.microsoft.com/en-us/answers/questions/629589/on-premise-exchange-2016-to-2019-migration-and-co
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