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I did this almost identical upgrade path a few months ago with the exception that I was using a built-in SQL Express database on the primary SolarWinds server which was using Server 2008 R2. I decided to do a new Server 2016 VM deployment (1 for the new SQL server and 1 for NPM) after reading a considerable number of posts on whether upgrading Server 2008 to 2012 or 2016 was a good idea.
The general consensus from sysadmins on Server Fault and Microsoft's forums was that it was a bad idea and it was much better to deploy a fresh VM and do a clean install. FYI, there is no direct upgrade between 2008 and 2016. In order to get there you would need to upgrade to 2012 first. It took a few days to configure the new servers manually, migrate the DB, migrate the NPM with SAM and then upgrade from 12.1 to 12.2. I was going to use new IP addressing for the new servers so I could do an almost zero downtime switchover but there were less complications by using the same IP addresses for the new servers. Less complications from my own internal tasks with changing DNS, User Access, ACLs etc and SolarWind's additional steps when migrating NPM and SAM to a new server with different IP addresses.
For me the steps were,
1. Deploy Microsoft SQL server (SQL Server 2016 Enterprise) to new NPM-DB VM (Server 2016)
2. Migrate the DB from SolarWinds NPM server to new NPM-DB VM
3. Migrate all SolarWinds products (NPM, SAM and NTA) to the new NPM VM server
4. Upgrade NPM to 12.2
5. Upgrade SAM to 6.5
Overall, it was pretty smooth with only two issues that had to be sorted out.
1. DB Error while executing script when running the Configuration wizard - Database configuration failed: Error while executing script- Cannot insert the value NULL into column IsGroupOfEntity, t…
2. The SolarWinds NPM 12.2 online installer will not allow you to deselect a product to upgrade. It upgrades all of them to the latest, so if you have a product that you do not want to update (or can't because you let the contract run out) , you have to uninstall that product in order to update from 12.1 to 12.2.
Only one issue with moving to the Server 2016 server in our Server 2008 R2 environment.
There is an issue with the Server 2016 communicating with the Server 2008 R2 WSUS server and downloading the updates. The server2016-template computer is seen in the WSUS management panel but the server gets the following error - (0x8024401c).
The 2017-10 Cumulative Update for Windows Server 2016 for x64-based Systems update on the Server2016-Template VM also did not fix the issue.
I ended up needing to use a script created by Adam Marshall that cleans the WSUS database and then optimizes the database by creating tables.
Other than that issue I had no issues with the 2008 to 2016 change, though I have had some experience with the Server 2016 so I did not have to go through any learning curve on the server GUI navigation and feature changes.