Upgrade path from small business server 2008 & what licenses do I need?

Question

I have a small business with ~15 users who are using a "desktop" style PC as a server. It's running "small business server 2008" and is acting as a file server and a (Microsoft) SQL server. There's no domain controller. The SQL database is just over 8GB and is growing. We've been told there's a 10GB limitation on database size with this edition of SQL server and that we need to switch to standard before the database gets that large.

I'd like to move to Windows Server 2019 and SQL server 2019, but I'm having some difficulty figuring out which editions I need, how many CALs, and which licenses. The likely target hardware is a "server" type machine with two six-core processors.

I've been advised by the company who supplies the software that uses the SQL database that I should run the database on one virtual machine and the file server on a second one. If we do that, there's another desktop PC I'd also like to virtualize and run on the new server (it's access using RDP by a few people).

Answer 1

Sounds like you'll need a Server 2019 Standard edition. If you plan to run hyper-v then Standard Edition provides rights for up to 2 Operating System Environments or Windows Servers containers with Hyper-V isolation when all physical cores in the server are licensed. For each additional 1 or 2 VMs, all the physical cores in the server must be licensed again.

As to SQL you can check some options here in case you can get by with SQL Express
https://learn.microsoft.com/en-us/sql/sql-server/editions-and-components-of-sql-server-2017?view=sql-server-ver15

Windows CALs are for either user or device server access. Some info here on windows CALS
https://www.microsoft.com/en-us/licensing/product-licensing/client-access-license

For the desktop virtualization
Windows Virtualization rights
Windows Virtualization Rights allow for a licensed device or user to access virtual Windows desktops
either remotely and/or locally, depending on how the device or user is licensed. You can license
devices or users for Windows Virtualization rights in the following ways:

• License devices with Software Assurance for the Windows desktop operating system or Windows
  VDA subscription on a per device basis via one of the following programs: Open License,
  Select/Select Plus, Microsoft Products and Services Agreement, Open Value, Enterprise
  Agreement, or Enrollment for Education Solutions.
• License users with Windows Enterprise E3/E5 subscription licenses or Windows VDA E3/E5
  subscription on a per user basis via one of the following programs: Open License, Select/Select
  Plus, Microsoft Products and Services Agreement, Open Value, Enterprise Agreement, or
  Enrollment for Education Solutions.

I'd suggest discussing these options with your resellers trained licensing specialist or contact a Microsoft Partner
https://www.microsoft.com/en-us/solution-providers/home

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Answer 2

For detailed information about the license issue, please call 1-800-426-9400, Monday through Friday, 6:00 A.M. to 6:00 P.M. (Pacific Time) to speak directly to a Microsoft licensing specialist. For international customers, please use the https://www.microsoft.com/en-us/licensing/worldwide to find contact information in your locations.

Answer 3

Hi @Heath Roberts ,

For SQL Server 2019 Edition, maybe you could chose Standard Server + CAL. Please refer to below illustration to chose SQL Server 2019 Edition:

There have 2 SQL Server 2019 licensing models, core-based licensing and Server+CAL licensing. It seems like you could chose Server+CAL licensing:

Please download the Microsoft SQL Server 2019 Licensing guide from attachment to get more information. For License issue, we suggest that you can consult professionals in this area. Please call 1-800-426-9400, Monday through Friday, 6:00 A.M. to 6:00 P.M. (Pacific Time) to speak directly to a Microsoft licensing specialist. For international customers, please use the https://www.microsoft.com/en-us/licensing/worldwide to find contact information in your locations. Or you can go to Volume Licensing Service Center support. Please choose region/language and choose to call or have web. People there will help you more effectively.

83153-sql-server-2019-licensing-guide.pdf

Best regards,
Carrin

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Answer 4

Any progress or updates?

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Answer 5

An in-place upgrade is never recommended and would be extremely risky. You couldn't upgrade directly any way which also adds another risk level.
https://learn.microsoft.com/en-us/windows-server/upgrade/upgrade-overview#which-version-of-windows-server-should-i-upgrade-to

I'd ask confirm here and with manufacturer about support for Server 2019
https://www.windowsservercatalog.com/

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