TFS2018 to AzureDevops 2019 Upgrade -Part 3

Table of Contents:
TFS2018 to AzureDevops 2019 Upgrade Part 1: Approach
TFS2018 to AzureDevops 2019 Upgrade Part 2: Create TFS Sandbox
TFS2018 to AzureDevops 2019 Upgrade Part 3: Upgrade sandbox instance to Azure Devops 2019 (this article)
TFS2018 to AzureDevops 2019 Upgrade Part 4 Upgrade production instance to Azure Devops 2019

In Part 1, I outlined the approach I had in mind to upgrade our TFS infrastructure. In Part 2, I narrated the steps to create a sandbox TFS instance. In this part, I will demonstrate the steps that were taken to upgrade that instance by installing AzureDevops2019. As of writing the URL for the installer is available at

Note: Prior to installation, I ensured with help from Data Center Operations that there was no way sandbox TFS instance (application and database tier) was able to communicate with production TFS instance. Moreover before the installation, I requested Data Center Operations to take a snapshot of the application and database tier virtual machines. The snapshots become handy if I have to revert and re-try the installation. I would strongly advocate taking a snapshot before proceeding with an important upgrade like Azure Devops.
Azure Devops 2019 installation took 35 minutes on sandbox instance.
After successful installation the application tier had to be restarted.
Following the restart, the below portal opened to configure Azure Devops (no more TFS!!)
I selected the second option (image below) since this was not a fresh installation but an upgrade to the existing TFS instance.
On the databases tab I did not select anything other than confirming that I had a backup… rest of the values were picked up by the configuration wizard.
On the deployment scenario confirmation tab I went ahead with Production Upgrade since this was a sandbox environment which didn’t interfere with production TFS instance. (I would select that option while upgrading production TFS instance as well)
Confirmed the login credentials for the service account for AzureDevops
Followed by configuring the application tier
Search option was disabled so there was nothing to do there. This was because Search was not installed in the previous version (TFS2018.Update2). This can however be configured after the rest of the application is configured and upgraded.
Same for Reporting and this too can be configured after the upgrade.
Once all the configuration settings had been updated, a confirmation page loaded up that listed all the values that were selected.
I verified that all was good and triggered a readiness check that ran for a couple of minutes.
All our XAML builds have been ported to task based build and release pipeline system a couple of years back and we were not using any XML builds. In case your team still is using, there is some helpful information provided here:

I acknowledged the warning and proceeded to Configure.
It took about 13 minutes to configure and another 13 minutes to upgrade for a database of size 1.7TB.
… and got the console view I was waiting for.
The super-awesome Azure Devops Server Administration Console.

It took less than 75 minutes to install, configure and upgrade the instance; way lower than what my previous few experiences have been working with TFS2010, TFS 2012, TFS 2015 and 2017 -if I remember right.

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