Migrating from SQL Server 2016/2019 to SQL Server 2025 or Azure SQL: A Complete Developer’s Guide

Rajesh Gami
Nov 06
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As databases grow and technologies evolve, upgrading your SQL Server environment becomes not just a good idea — but a necessity.
With SQL Server 2025 and Azure SQL, Microsoft brings major improvements in AI-powered query performance, security, vector indexing, and integration with cloud intelligence.

If you’re still running SQL Server 2016 or 2019, this article will help you understand the migration process, tools, risks, and best practices to move your data safely and efficiently.

1. Why Upgrade to SQL Server 2025 or Azure SQL

Upgrading isn’t just about new features — it’s about future readiness, performance, and security.

Benefit	Description
AI-Powered Query Optimization	SQL Server 2025 automatically tunes queries using adaptive learning.
Vector & Embedding Index Support	Enables Retrieval-Augmented Generation (RAG) workflows for AI apps.
Better Security & Encryption	Always Encrypted with Enclaves, row-level access control, and ledger features.
Cross-Platform Deployment	Run SQL Server on Windows, Linux, containers, or Azure seamlessly.
Seamless Cloud Integration	Direct link to Azure Synapse, Power BI, and Azure AI.
Zero-Downtime Upgrades	With distributed availability groups and online index rebuilds.

2. Migration Options

Before starting, decide whether you want to:

Upgrade On-Premise SQL Server (to 2025)
→ Keep your existing hardware or virtual machines, just upgrade binaries and data.
Migrate to Azure SQL (Platform-as-a-Service)
→ Move database workloads to cloud-managed SQL with automatic updates and scaling.
Hybrid Model (Best of Both)
→ Keep sensitive data on-premise, sync analytics or reporting to Azure.

3. Migration Planning Workflow

Below is the flowchart showing the end-to-end process of migrating from older SQL Server versions to SQL Server 2025 or Azure SQL:

Migration Flow Diagram

(On-Prem SQL 2016/2019 → Assessment → Compatibility Fixes → Backup/Export → Restore or Import → Validation → Optimize)

┌────────────────────────┐
│   SQL Server 2016/2019 │
└──────────┬─────────────┘
           │
           ▼
┌────────────────────────┐
│ Assessment & Discovery │
│ (DMA, Azure Migrate)   │
└──────────┬─────────────┘
           │
           ▼
┌────────────────────────┐
│ Fix Compatibility Issues│
│ & Deprecated Features   │
└──────────┬─────────────┘
           │
           ▼
┌────────────────────────┐
│   Backup / Export DB   │
│ (BACPAC / DACPAC / .bak)│
└──────────┬─────────────┘
           │
           ▼
┌────────────────────────┐
│ Restore to SQL 2025 or │
│ Import to Azure SQL     │
└──────────┬─────────────┘
           │
           ▼
┌────────────────────────┐
│ Validate Data & Tests  │
│ (Schema, SPs, Triggers)│
└──────────┬─────────────┘
           │
           ▼
┌────────────────────────┐
│ Performance Optimization│
│ (Indexes, Statistics)  │
└────────────────────────┘

4. Step-by-Step Migration Process

Step 1: Assess Current Environment

Use Microsoft Data Migration Assistant (DMA) to:

Detect compatibility issues
Identify deprecated features (e.g., TEXT, NTEXT)
Get recommendations for SQL 2025 or Azure SQL
Evaluate database size, dependencies, and collation settings

Command

DataMigrationAssistant.exe /Assess /SourceConnection:"Server=oldSQL2016;Database=MyDB"

Step 2: Fix Compatibility Issues

Common issues when migrating from 2016/2019:

Deprecated data types (TEXT, NTEXT, IMAGE)
Breaking changes in T-SQL syntax
Non-deterministic functions in indexes
Unsupported features in Azure SQL (e.g., cross-database queries)

Example Fix

-- Old (Deprecated)SELECT * FROM Users WHERE CONVERT(TEXT, Name) = 'Rajesh';

-- New (Supported)SELECT * FROM Users WHERE CAST(Name AS NVARCHAR(MAX)) = 'Rajesh';

Step 3: Choose the Right Migration Tool

Tool	Best For	Description
Data Migration Assistant (DMA)	Compatibility & assessment	Scans schema and recommends fixes
Azure Database Migration Service (DMS)	Full cloud migration	Automates migration from on-prem SQL to Azure
BACPAC / DACPAC	Schema + data export	Lightweight way to move smaller databases
Transactional Replication	Near zero downtime migration	Replicates changes during transition
Log Shipping / Always On AG	Large enterprise migrations	Keeps old and new DBs in sync during cutover

Step 4: Backup or Export Database

For on-prem upgrades:

BACKUP DATABASE MyDB TO DISK = 'D:\Backup\MyDB.bak';

For Azure:
Export to a BACPAC file:

SqlPackage.exe /Action:Export /SourceServerName:oldSQL2019 /SourceDatabaseName:MyDB /TargetFile:MyDB.bacpac

Step 5: Restore or Import

For SQL Server 2025 (On-Prem):

RESTORE DATABASE MyDB FROM DISK = 'D:\Backup\MyDB.bak' WITH MOVE 'MyDB_Data' TO 'D:\SQLData\MyDB.mdf';

For Azure SQL:

SqlPackage.exe /Action:Import /TargetServerName:<AzureServer> /TargetDatabaseName:MyDB /SourceFile:MyDB.bacpac

Step 6: Validate Schema and Data

Once restored:

Compare table counts, views, and stored procedures
Run DBCC CHECKDB for consistency
Execute sample queries to ensure performance

Example Validation:

SELECT COUNT(*) FROM dbo.Users;
DBCC CHECKDB(MyDB);

Step 7: Optimize for SQL 2025 or Azure

After migration:

Rebuild indexes for new optimizer stats

EXEC sp_MSforeachtable 'ALTER INDEX ALL ON ? REBUILD';

Enable Query Store to monitor query performance
```
ALTER DATABASE MyDB SET QUERY_STORE = ON;
```
Review AI-assisted performance tuning reports (new in SQL 2025)

5. Migrating to Azure SQL: Extra Considerations

Moving to Azure SQL is not a simple lift-and-shift — it’s a paradigm shift.

Consideration	Explanation
Networking	Use private endpoints and VNET integration
Authentication	Migrate to Azure AD-based logins
Backups	Automatic in Azure (7–35 days retention)
Jobs	Replace SQL Agent jobs with Elastic Jobs or Logic Apps
Monitoring	Use Azure Monitor, Log Analytics, and Query Insights

6. Common Migration Challenges

Issue	Cause	Solution
Collation mismatch	Different collation between old and new DB	Align collation before restore
Unsupported features	Cross-database queries, CLR, etc.	Refactor or use Elastic Jobs
Authentication errors	SQL Logins not mapped	Migrate logins using `sp_help_revlogin`
Performance drop	Old statistics and indexes	Rebuild indexes and update stats
Downtime	Live production workloads	Use DMS or Replication for cutover

7. Post-Migration Checklist

✅ Verify all tables, triggers, stored procedures
✅ Validate foreign keys and indexes
✅ Reconfigure jobs, alerts, and linked servers
✅ Run load testing
✅ Enable Query Store & Performance Insights
✅ Monitor resource utilization for 7–14 days

8. Example Hybrid Migration Scenario

Imagine an organization like Phoenix Air Repair Inc. using SQL Server 2016 on-prem for ERP, and migrating analytics to Azure SQL for Power BI.

Workflow

Keep operational DBs on-premise (SQL 2025)
Replicate data nightly to Azure SQL using Azure Data Factory
Connect Power BI and Azure Synapse for analytics
Achieve hybrid speed + cloud scalability

10. Conclusion

The future of databases is intelligent, secure, and connected.

Whether you choose on-prem SQL Server 2025 or cloud-native Azure SQL, the key is a strategic migration plan backed by testing, automation, and monitoring.