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Ugrade In-Place from 2014 Enterprise to 2019 Standard

Hi experts. My client plans to perform an in-place upgrade from their 2014 Enterprise Edition to 2019 Standard I'm not sure you can move down in Editions, just wanted to get your ideas. Thanks

Of course you'll first need to run the free MS to check for possible issues with Enterprise-level things in the dbs that can't be converted down.

I personally would never do in-place on this. Instead, install a new clean 2019 and copy the data to the new version. I don't know in theory if you can do it or not. If you try, good luck with it ... you'll need it.

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It is not supported - according to this document: https://docs.microsoft.com/en-us/sql/database-engine/install-windows/supported-version-and-edition-upgrades-version-15?view=sql-server-ver15

Since it is not supported - this is going to require a new clean install. If the concern is that connection strings need to be updated - there are other methods to handle that issue (DNS, server alias, client alias, rename server, etc.).

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I agree with both comments and I appreciate your feedback. Yes they have big concerns about connection strings. So we have Server1, we build Server2 with SQL 2019 and restore databases, jobs, logins etc to Server2. Then if we disconnect the NIC on Server1, rename Server2 to Server1 -- would that work?

Typically you use CNAME entries that will point the old connections to the new servers. I don't know any more details than that (I'm a DBA not at all a network person) but we have changed our server/instance names, including named instances, several times and our older code referencing older names continues to work.