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A
Although there aren't quite as many core Microsoft Enterprise products leaving support this year and and next as there were last year, there are still some major ones that really need to be on your radar. SQL Server 2016 and 2017 are both leaving extended support in July 2026 and October 2027, respectively. That might seem like it's a long way away, but customers really do need to be planning now, as these products, if they are unpatched, will be increasingly vulnerable to all kinds of attacks. But you've got lots more options and considerations other than moving just to SQL Server 25 automatically. And today's guest is here to walk you through what you should be doing next. Welcome to the Directions on Microsoft Briefing podcast. I'm Mary Jo Foley, the editor in chief here at Directions. I'm your host for the series of podcasts for those interested in the Microsoft Enterprise IT ecosystem. My guest today is Directions Analyst Andrew Snodgrass. Andy analyzes and writes about Microsoft's data management, business intelligence, and machine learning solutions, as well as aspects of licensing. Before he joined Directions on Microsoft, Andy was vice president of IT for a global Fortune 500 company, where he directed overall IT activities and strategy for the company's global operations. Hi Andy, thank you so much for doing the podcast today.
B
Always a delight to be here. Good.
A
It's been a while since I've had you on, so I'm excited.
B
I know, I thought you were upset with me, but maybe not.
A
No, no, no, not at all. Let's get you going by starting you with explaining some of the challenges when it comes to planning for a SQL Server migration. I know you're in the midst of writing a whole series of reports for us at Directions on this topic, but in the first one you talk about the fact that SQL Server is used for just managing databases, and that's what adds complexity to this migration task.
B
It really does. For most people when they think of SQL Server, they think of the databases. Without a doubt, that's the largest part of why people use SQL Server. But over the years, and by years I mean decades, the product was expanded. And it's got more than just database components in it. There's an integration component called Integration Services, and it does what we call etl. It pulls data from one location, transforms it, and puts it into another one. It's the way you populate data marts and data warehouses. It also has a couple of BI components in there, business intelligence stuff. There's a thing called Analysis Services for creating data models that you use in a lot of different areas. And then there's reporting services for actually generating reports. And these things people have been using literally for, for decades now. They work with SQL Server databases, but the cool thing about them is they also have the ability to work without SQL Server databases. So they can grab data pretty much from anywhere and transform it or integrate it, or generate reports. The main point is that literally over the last few decades, customers have used the various components to build thousands of processes and applications. What that means from a management standpoint, when somebody says we're upgrading SQL Server, that you really ought to pay attention to is that it's more than just upgrading a database. 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.
A
Makes sense. It seems like there are a couple of key choices that customers have to start out figuring out. They either stay on SQL Server or they could go with a competitive product. The other thing they have to think about, of course, is whether they want to be on Prem or in the cloud. If you figure those things out, are we all done? Is it that simple or not really.
B
I must have made a mistake in the report I wrote. If it made it come out thinking that it was that simple.
A
I love trying to simplify complex things.
B
Everything's simple in the planning phase. As long as you're not the one implementing it, it's no big deal.
A
That's true.
B
But actually it really does come down to those few key decisions. It's the product and the location. Now, if you remember, we're talking about SQL Server 2016 and 2017 here. We need to put on our way back goggles and take a look at things. Ten years ago, ten years ago, SQL Server had very few challengers. Mostly it was like Oracle Database and a couple of. And between those two, you were still writing traditional relational database applications. That's what SQL Server is really known for, this high scale OLTP capabilities of big transaction stuff. Now what we have, fast forward 10 years is we have PostgreSQL, really good option, high scale, good competitor SQL server. But we also have all these no SQL databases that really came to fruition during that time. Which means there could be a better database solution for the application that you developed 10 years ago and use SQL Server for. And then the same is true for the other components, both with integration services and the BI stuff, the modeling and the reporting. There are solid competitors out there. That may be worth exploring. Now, those are things to take a look at. But one of the cautions I would say on that is changing products can be a lot of effort and you don't want to underestimate the amount of time it would take to rebuild a database or all the applications or the business processes and everything else going on. This is a non trivial effort to say we're going to switch to a product. There's also this thing about the cloud and if we go back 10 years ago, the cloud was growing, but it wasn't the de facto choice for a lot of customers. Now there are lots of cloud options out there that may be more attractive than staying on prem. There's quick deployments, quick scaling, there's all kinds of reasons why the cloud has got some really attractive capabilities going on. But we need to remember that the applications that are using SQL Server 2016 and 17 were built for a different time. And 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. We need to take into account the decade that is passed during this time and say where do we want to go into the future? So I'm sorry if I oversimplified it there in the report, but it's really a matter of this is a time to really look introspectively and say, what do we do next?
A
A perfect inflection point for customers. Speaking of simplification, here's something I know that's not going to be simple licensing. If you decide to go with cloud or an Azure based option when you're doing your migration, I'm sure there are many licensing considerations you have to take into consideration. Walk us through at least a couple of those.
B
Right? Well, I'll take you to a couple because I think there's really not that many. Yeah, the nice thing with SQL Server is that when you bought 2016, 10 years ago, whenever it was, it's a perpetual license. And so you have the indefinite right to use this forever and ever. Even after it goes past extended support, you still own the rights to use it. So you could keep using it unprotected. That's, you know, I know people that do that kind of thing. I don't recommend it, but you know, it's an option that's out there. But one of the things that a lot of customers tend to do with SQL Server in particular is they carry a thing called Software Assurance. And so if your IT departments are the type where you've carried this essay is what it's called Software Assurance. There's a reason for that. You pay a certain amount every year. It's like 25% of the original cost. And that gives you certain benefits. One of the main benefits off of that is the right to upgrade to a newer version. Okay. So you don't have to rebuy the license, you can just upgrade to the next one. But it also gives you some special benefits if you're moving to the cloud. There's two of them there that if you're looking in this direction that I would really say take a look at. The first one is called License Mobility. This allows you to take an on PREM license, a SQL Server license that you have, and reassign it to virtual machines that are running either in Azure or another cloud provider. There's variances that are there, whether it's Google or AWS or another third party. And of course, all the real benefits, the best benefits, are all reserved for Azure. So if you want to just lift and shift, there's a way of preserving the investment that you have on PREM and reassigning that license to workloads that happen in the cloud, which is a nice thing to do, preserve your investment. Right?
A
Yeah.
B
There's also a thing called an Azure Hybrid benefit. What this lets you do is you can take your on PREM SQL Server license and, and say that you're applying it to an Azure service and there's particular Azure services that you can do this with. And what it will do is give you a discount on that Azure service. So, for example, we want to take SQL server on prem 2016 and we want to move this to an Azure SQL managed instance deployment. What that'll do is give me a discount on Azure SQL Managed Instance. And the discount that I get there is more than the software assurance price that I've been paying on prem. Okay. And so it's really something 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.
A
Nice. All right, I am going to pause here and take a quick break so I can talk about why you should make it a priority this year to attend one of our directions on Microsoft licensing boot camps. And Andy just came back from the last one, so I know he agrees here.
B
Well, I was going to say that's kind of like the main attraction. Right. Is that I'm going to be there.
A
Exactly.
B
And we go for rides. Yeah. If you go to one of these.
A
All right. So as of November 1st last year, Microsoft eliminated tiered volume discounts for online services in the EA and the customer Agreement or mca. Unless you are prepared, this change means you are facing a potential 6 to 12% price increase on your core Microsoft cloud services like Microsoft 365, Azure and Dynamics 365. So what can you do? You have a defense Invest in Microsoft licensing expertise. The way to do that Come to the Boot Camp. Our next in person directions on Microsoft Licensing Boot Camp is in Washington D.C. from April 28th to 30th, 2026. You should send your IT procurement and ITAM leaders so they can learn about the new Microsoft licensing reality. Everyone there learns how to control your Azure consumption costs so you can cut your largest Microsoft cloud spend component. We'll also help you master the strict licensing rules for high cost products like Copilot and Microsoft 365 add ons while you maintain compliance and maximize your organization's ROI without overbuying. And we'll also help you craft a tailored framework for your renewal strategy so you can secure concessions that will offset those lost volume discounts. To get your spot reserved today to directions on Microsoft.com training, you'll get to talk to Andy, Wes and our other Directions licensing experts there. And if you can't make it to DC in April, you still can go to our next in person boot camp in Chicago in September or one of our virtual licensing boot camps as well. Okay, back to SQL Server Migration prep with Andy. Okay, speaking of migration, I noticed in one of your reports you said migration is not the same as upgrading. So I was curious about that. Talk a little bit more about what you want customers to know about that.
B
Okay. What's going to do this from a management perspective? It's a little bit technical, but understanding the difference between migration and upgrading in my mind is one of the greatest benefits of using SQL Server. And I'll give you an example to explain it. I suppose we have a database that we built in SQL Server 2016. Now, 10 years ago, SQL Server had certain data types that were available then. It had a query engine that was optimized for back then. Most importantly though, when we built this database, it worked with applications at the time and it still does. We have applications that are dependent on the way that this SQL Server 2016 database works and Maybe this whole thing was some kind of application and database that we had to get certified by a regulatory agency and signed off policy agreements. Whatever it is, the whole thing is packaged up. It works under SQL Server 2016. But now SQL Server 2016 is retiring, and so we have to move this database to a newer version. My question is, do we have to rewrite our apps? Do we have to get recertified? Do we have to make all these changes? The answer is no, we don't. And here's why. It's because we can deploy a new SQL Server 2025 or 2022 or 2019 if we want, and we can move that 2016 database over using backup and restore. And when we do that, we will tell SQL Server 2025 to pretend that it's a 2016 installation. Whenever it works with this particular database, doesn't matter about the rest of them that it's managing. But on this database, I want you to pretend you're a 2016 install. And that's because SQL Server has this rather unique feature, and it's called compatibility mode. And what it does is allows it a diversion to pretend that it was a previous version. And right now, 2025 goes all the way back to, I think it's 2014 or 2012. I mean, it goes back a long way. What that means is we can bring over that datab, put it on this new server where it's protected, but still have it run like it did 10 years ago. Which means all of those apps continue to work and all those certifications are still applicable. And because we don't have to upgrade the database, we can leave it just as it is. We don't have to spend all the time and effort of going through and testing and revalidating everything else to recognize all the changes that have happened in the last 10 years.
A
Nice.
B
Compatibility mode is one of the greatest time savers ever.
A
Very cool. I had never heard about that. That's cool.
B
Well, you know what? And that's like one of the things I keep preaching is take a look at this. Migrating is not the same as updating. Right?
A
Okay.
B
Yeah.
A
All right. Let's talk about a controversial topic. ESUs extended CDC. I know, sorry. People are going to ask, you know, I know. We already know they're going to be available for customers who are on SQL Server 2016 who are not yet ready to move when. When support ends. So I'm curious what you think, should enterprises consider buying them when they're looking at options to get off SQL Server 2016? Or no.
B
So these extended security updates, what they allow you to do is you can keep running SQL Server securely and supported for up to another three years past end of extended support. Right, right. But they're expensive.
A
Yes.
B
The first year you'll have to pay 75% of your original purchase price. The second year is 150%, and the third year is 300%. So they're really, really expensive for you to do this. If you did it for the whole three years, then what is that? That's 400, 525% of what you originally paid for it. It's an increasing amount of money on it. And if you think about what we just talked about with compatibility mode, you know, if I have an existing database, why don't I just move it to a new server and keep running it the way it was? There are very few cases where this makes sense, but where they do, people are willing to pay for them. And I think it would be a scenario where you didn't plan properly is what it really comes down to is if you have an application or database that you know is going to be retired, but you need a little more time to get it done or to move it over. Like if you had a power plant and you're gathering telemetry data from a bunch of substations. Now, obviously this is a critical environment. It's under regulatory control and everything else. And if your migration that you should have planned earlier isn't done by, let's say this July, then you may need to buy some ASUS to keep everything from failing for another year until you finish your migration. Right.
A
And you can buy them for just a year. Right. You don't have to go all three?
B
No, you don't have to go all three. You have to buy them in successive years on it. Yeah. And 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.
A
Yeah.
B
I mean, you had better really screwed up planning in order to say that this is a good idea, or there might be a really good justifiable reason for doing this. Suppose you had a little regulatory database that was out there that you had to have on these servers that was running just fine and your company's growing dramatically in other areas. And so you turn all your people to focus on the new growth and you've got stellar margins and profit and everything else coming in. You know, spending 150% original purchase price on a 16 core server that might Be okay. I mean, it might. Might be a rounding area error. Right? Let's just ignore this for another year or two. So there are reasons to do ESUs, just not many. And usually it's because you didn't do enough planning ahead of time.
A
Okay.
B
Yeah.
A
All right, so say a customer is good at planning, and they want to create a checklist for the end of Support of server 2016 or 17. What would you say has to be on that checklist?
B
So you have to start with an inventory of all your SQL Server instances. And I don't just mean the 2016, 2017 ones, I mean all of them. And clean up your data architecture or the design for your have. For your data state or whatever it is. And this inventory needs to have the versions of all those SQL Server instances and their usage metrics. The reason is most organizations will have multiple versions in place across their organization. And by knowing what versions we have and the usage metrics, we may be able to find places where we can move stuff and we can simplify our whole environment by migrating databases off of 2016 onto newer SQL Server versions that have room. Now, remember, we can migrate, not just upgrade. Right. I might have some 2019 servers out there that I deployed. Enterprise edition, whatever it is, 64 cores. And let's say I'm using it at 70% of capacity. You know, it's hard to physically change the compute infrastructure within a server, so we're sitting there with 30% unused capacity on it. I got a couple of these 2016 servers over here with databases. Which ones can I move onto this thing without taking it over 100%? What I'm looking at is anytime you come into a retirement event like this is always a good time to look at optimizing the environment. And that thing means moving stuff to different servers, load balancing, making sure some deployments haven't reached their max, making sure that sums aren't underutilized. You always have to look over your entire data state and all the existing servers. Then what you need to do is plan a migration for each application separately. Now, some applications require multiple databases, so you got to look at them together. Most of the time, what we find on SQL Server instances is that it'll have hundreds or even thousands of databases that are there that are. Sorry, dozens or hundreds. I've seen thousands, but dozens or hundreds. Yeah, I know, right, but you'd have thousands of databases over a tiny environment. But a server might have dozens or even hundreds different ones, different sizes. Right. Where's the best place for these things to reside going forward, you might already have some capacity on it, or you may want to stand up a new environment and consolidate maybe two servers onto a single one. You know, because the other aspect on this is hardware has changed. And so what the hardware that you had 10 years ago where you said, ah, this is kind of maxing out now, you got processors that will do double what they did 10 years ago. You got improved storage devices. You might be able to take two servers and move them onto one and actually cut the number of licenses that you have. I mean, there's. This is a 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.
A
I like your silver lining approach here. Don't look at it as a negative that these things are expiring. Look at it as an opportunity.
B
It is. Well, all right, so let me give you a little background on that. I came from an industry with 2 1/2% margins.
A
Yikes. Okay.
B
Right, Yikes. So 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.
A
Nice. All right, well, thank you so much for all the great advice, Andy. Really good stuff.
B
You bet.
A
I would like to remind our listeners they can find lots more coverage of all things Microsoft related on directions on Microsoft.com thank you so much for listening. If you have questions, comments, or any topics that you would like to hear the Directions analysts cover in one of these podcasts, please do not hesitate to contact me via X or BlueSky. Directions on Microsoft is also on LinkedIn, so make sure you follow us there too. And give us a follow at DirectionsMSFT on X or directions on Microsoft on BlueSky for all of the latest Microsoft Enterprise product and licensing information. Thanks again,
B
Sam.
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
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.
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For more Microsoft enterprise migration strategies and licensing insights, visit Directions on Microsoft’s website or follow their social channels.