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Is possible to run swing migration from SQL SERVER 2008 R2 to 2019 with Log Shipping?

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Yes, It's possible.

You can migrate databases from older versions like SQL Server 2008 R2 to SQL Server 2019.

Check answer from here. Migrate to SQL Server 2019

Log shipping: Log shipping is supported if primary is running SQL Server 2008 SP3 or later, or SQL Server 2008 R2 SP2 or later, and secondary is running SQL Server 2019.

Warning: If an automatic or manual failover happens and the SQL Server 2019 instance becomes primary, SQL Server 2008 or SQL Server 2008 R2 instance becomes secondary and cannot receive changes from primary.

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