Podcast Summary: SQL Server Migrations – Tips to Help You Prepare

Podcast: The Directions on Microsoft Briefing Podcast
Episode: SQL Server Migrations: Tips to Help You Prepare
Host: Mary Jo Foley (A)
Guest: Andrew Snodgrass (B), Directions Analyst
Release Date: February 12, 2026

Episode Overview

This episode dives deep into SQL Server migrations as versions 2016 and 2017 approach their end of extended support (July 2026 and October 2027, respectively). Host Mary Jo Foley interviews Directions on Microsoft Analyst Andrew Snodgrass, exploring the technical and strategic complexities of moving business-critical SQL Server workloads, navigating upgrade and migration choices, licensing considerations, and how organizations can use this transition as an opportunity to optimize data environments and costs.

Key Discussion Points

1. The Complexity of SQL Server Migrations

[02:00–04:13]

• SQL Server is not just databases—it includes Integration Services (ETL), Analysis Services (BI modeling), and Reporting Services.
• Organizations have built thousands of business processes and apps atop these components, making migrations much more than a simple database upgrade.
• “This involves looking at business processes, independent applications, and all kinds of things that go along with that. And there’s a lot of moving parts in it. That’s why upgrading SQL Server can be a risky and complex operation to deal with.” – Andrew Snodgrass (B), [03:50]

2. Core Choices: Product & Location

[04:13–07:44]

• Decisions hinge on whether to stick with SQL Server or move to a competitor (PostgreSQL, NoSQL options), and whether to stay on-premises or move to the cloud.
• The IT environment is very different from when most existing SQL Server deployments were architected (10+ years ago).
• “With all these other options, customers also have internal strategies and objectives and architectures for IT deployments that make use of modern concepts. And so this whole idea of are we going to move from here and is it this easy decision of, well, do we stay with this product or we go to the cloud? It’s more than that.” – B, [06:47]

3. Licensing When Migrating to Cloud or Azure

[07:44–10:51]

• SQL Server 2016/2017 licenses are perpetual, but Software Assurance (SA) is crucial for value:
  • License Mobility: Lets you move existing on-prem licenses to VMs in Azure or other clouds.
  • Azure Hybrid Benefit: Apply on-prem licenses to Azure managed services for discounts — these discounts can be more than the ongoing SA price.
• “If you have these licenses, there are ways to leverage these things going to the cloud so that you don’t lose your investment and can actually get some discounts going forward.” – B, [10:36]

4. Migration vs. Upgrade: Exploiting Compatibility Mode

[13:19–16:12]

• SQL Server’s compatibility mode enables you to restore older databases onto newer SQL Server versions (e.g., move 2016 DBs to 2025), with the instance “pretending” to be the older version for that database.
• This enables seamless app support, regulatory compliance, and avoids recertification or wholesale app rewriting.
• “Compatibility mode is one of the greatest time savers ever.” – B, [15:58]

5. Should You Buy Extended Security Updates (ESUs)?

[16:14–19:27]

• ESUs provide up to 3 years of supremely expensive post-support security coverage (Year 1: 75%, Year 2: 150%, Year 3: 300% of original cost).
• ESUs are “usually because you didn’t do enough planning ahead of time.” They’re a last resort for critical regulated apps or delayed migrations.
• “If you did it for the whole three years… that’s 525% of what you originally paid. Microsoft doesn’t want you to do this either… you had better really screwed up planning in order to say that this is a good idea.” – B, [17:00/18:38]

6. End-of-Support Preparation Checklist

[19:29–22:46]

• Inventory: List all SQL Server instances and versions—not just the ones at risk.
• Usage Metrics: Identify underutilized capacity—migrate and merge workloads where possible, leverage newer hardware for consolidation.
• Migration Planning: Treat each application separately, especially those with multiple databases; plan placement on new or existing infrastructure.
• “Anytime you come into a retirement event like this is always a good time to look at optimizing the environment... This is one of those events where you really should relook at everything that you’re doing and try to optimize rather than just shuffle it off to what we did before.” – B, [22:28]

Notable Quotes & Memorable Moments

• On Planning Complexity:
  “Everything’s simple in the planning phase. As long as you’re not the one implementing it, it’s no big deal.” – B, [04:45]
• On Usefulness of Compatibility Mode:
  “Migrating is not the same as updating. Right?” – B, [16:12]
• On ESUs as a Planning Failure:
  “Microsoft doesn’t want you to do this either. That’s why in the third year they’re going to charge you 300% of original cost.” – B, [18:38]
• On Opportunity in Upgrade Events:
  “Every time I look at this, I’m like, where can I save some dollars? I want to save some pennies here and there. And so I kind of look at that as an opportunity.” – B, [23:03]

Key Timestamps

• 02:00 – Complexity of SQL Server and migration challenges
• 04:13 – Core product/location choices: stay, move, on-prem, or cloud?
• 07:44 – Cloud migration and key licensing benefits
• 13:19 – Difference between migration and upgrade; compatibility mode explained
• 16:14 – ESUs: what are they and when to use them (or not)
• 19:29 – End-of-support migration/optimization checklist
• 22:46 – Reframing end-of-support as an opportunity for improvement

Actionable Advice for SQL Server 2016/2017 Customers

• Start inventorying and planning migrations now—don't wait for extended support to end.
• Leverage Software Assurance and explore License Mobility and Azure Hybrid Benefit to preserve and optimize investments.
• Exploit compatibility mode to migrate with minimal disruption, especially for legacy applications needing stability or certification.
• Use the end-of-support event to optimize architecture: consolidate, right-size, and modernize your data environment.
• Only consider ESUs as a true last resort—they are costly and intended for exceptional circumstances.
• Engage experts and training (e.g., Directions on Microsoft Boot Camps) to navigate tricky licensing and migration waters effectively.

For more Microsoft enterprise migration strategies and licensing insights, visit Directions on Microsoft’s website or follow their social channels.