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As documented, A backup taken on SQL Server 2008 (10.0.x) and later, can be restored to SQL Server 2019 (15.x) without changing its compatibility level, as long as the database backup has a compatibility level of 100 or higher.
Your best option is to take a native backup on prem and restore it to RDS. You can then run your test application with the RDS database to check for any possible compatibility issues.
Hello.
Option 1: Should I upgrade the on-prem to a supported version, say SQL 2014 and then migrate to Amazon RDS?
AWS DMS supports using Microsoft SQL 2008 as a source database.
So it doesn't necessarily seem like an update is necessary.
https://docs.aws.amazon.com/dms/latest/userguide/CHAP_Introduction.Sources.html
Option 2: Is there a tool that can run checks against on-prem 2008 SQL server and a supported version in Amazon RDS to suggest possible migration failure? This way if the tool comes clean then I don't have to upgrade the on-prem server. I can then do a database dump and import in RDS. Is this feasible?
You can also check whether migration is possible by using AWS DMS.
It is possible to confirm the feasibility of migration to some extent by creating an AWS DMS migration assessment report.
https://docs.aws.amazon.com/dms/latest/userguide/CHAP_Tasks.AssessmentReport.html
https://docs.aws.amazon.com/dms/latest/userguide/CHAP_Tasks.AssessmentReport1.html
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