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This technical paper provides an in-depth analysis of the "certificate chain was issued by an authority that is not trusted" error when connecting to SQL Server in Azure environments. The article examines SSL/TLS encryption mechanisms, root causes including self-signed certificates, encryption default changes, and certificate validation processes. Multiple solutions are presented for different scenarios, including temporary workarounds and long-term best practices, accompanied by detailed code examples and configuration instructions. The paper also explores breaking changes in Microsoft.Data.SqlClient library and their impacts, offering comprehensive troubleshooting guidance for developers.