SSRS upgrade in place 2016 to 2019

Thanks again Joy. The details about what is in the RS database is helpful. I will summarize my plan and ask a couple of final questions for the in-place upgrade.

A. I will backup all my database including both SSRS databases.
B. I will backup the SSRS encryption keys to a file and I noted all setting and values for all tabs in the SSRS configuration manager.
C. I will upgrade in-place my DBMS from 2016 to 2019 (do I use the checkbox and allow this upgrade to uninstall the existing SSRS at the same time?)
D. I will install the new SSRS download
E. I will restore both SSRS database and the encryption key.

My final questions are?

1. Will I need the RSReportServer.config file or any of the config files I see on the current SSRS install in C:\Program Files\Microsoft SQL Server\MSRS13.MSSQLSERVER\Reporting Services. Should I backup and possible replace any of the files after the new SSRS installation.
2. Do I use the checkbox and allow this upgrade to uninstall the existing SSRS at the same time as the DBMS upgrade, or do I uncheck this, and can the new SSRS install coexists with the original?

I will upload a few screen prints.

Hi @Anthony Curreri ,
Upgrade to Reporting Services 2017 and later from Reporting Services 2016 and older isn’t the same upgrade scenario as in previous versions. When upgrading to Reporting Services 2016 and older versions, you could following an in-place upgrade process using SQL Server installation media. When upgrading to Reporting Services 2017 and later from Reporting Services 2016 and older, you can’t follow the same steps because the new Reporting Services installation is a standalone product. It's no longer part of the SQL Server installation media.

To upgrade from Reporting Services 2016 and older versions to Reporting Services 2017 and later, follow the Migrate a Reporting Services Installation (Native Mode) article, with Reporting Services 2017 or later as your destination instance.

If you still have any question, please feel free to let me know.
Best Regards,
Joy

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Thanks Joy.

I had read these steps and similar documentation before posting. I re-read this document. My questions are specific and I'm hoping for someone with experience could fill in the details not really covered in these documents.

I am upgrading in-place, same server, the SQL Server DBMS that supports a third party product that uses SSRS with reports created also.
This upgrade is from 2016 to 2019 and warns that reporting services will be uninstalled
This is not a side by side migration and my questions are all related to the new SSRS install, the old SSRS uninstall, and the report migration all being on the same server. I have no test server for this, so I cannot roll the dice.

Regarding MIGRATING reports - THIS IS MY CONCERN. I read a little about rs.exe and I see there is a option to uninstall Reporting Services. It's not clear to me how to migrate the reports, and not lose them, when everything is on this same server. What am I actual migrating? from where to where? that lives outside the DBMS, RDL files? Other?

Can someone please add some clarity on this Migrating your reports step, what I am really doing and how I can be successful all on the same server?

If I omit the Uninstall checkbox option will I have 2 SSRS installs on this server?
Will I really need to restore the before version of Report Server & ReportServerTemp? The existing ones will still be valid after my DBMS upgrade, will the SSRS new install, on the same server, overlay or damage them in any way?
Will I have two version of SSRS installed until one is removed?

Thanks,
Tony