Side by side migration of MSSQL and SSRS from 2008 to 2019

[HuwDG]

I have a MSSQL 2008R2 database server which hosts our legacy application databases along with the ReportServer and ReportServerTempDB databases for a SSRS 2008 instance. The SSRS instance itself is running on separate host.

We wish to migrate the database and SSRS servers to new hardware running MSSQL2019 and SSRS2019 with the same configuration of the database server hosting the ReportServer databases with the SSRS 2019 instance running on a different host.

I think I'm fairly comfortable migrating the logins, agent jobs and application databases :
script out the logins, restore the databases, script out the agent jobs.

However, I am struggling to find a workable approach for the SSRS side of things. One suggestion I've read is to install SSRS 2019 on the new server and just restore the ReportServer databases and encryption key from the old environment. My worry about this is if there is anything specific to 2019 (or earlier) in the SSRS2019 version of the ReportServer databases, and that SSRS 2019 would be not happy with what is essentially a "2008 version" of its repository.

Another approach is to migrate the reports and subscriptions one at a time (500+ reports, some with over 100 subscriptions, although only about 70 reports are used regularly).

Could anyone recommend a viable approach for this type of migration/upgrade (or confirm whether a certain approach definitely wont work).

If migrating the reports one at a time is the only way, could someone please advise how the subscriptions can be copied over.

Many Thanks

[#2]

@HuwDG A bit of time has elapsed since you posted this.  Did you manage to complete this migration? I'm facing the same task in the very near future.  If you have any tips from your experience, I would be grateful.  TIA

[#3]

@NZ_Endo 

Hi, sorry about the delay in responding, the project was delayed until the new year in order for other projects to go through first, but I am back on it again.
After several tests I have confirmed that my SSRS 2008 instance can talk to and is happy with its ReportServer database being on a SQL 2022 instance, with that in mind, In order to de-risk the upgrades/migrations I am doing it in a 2 phase approach:

Phase 1. (very soon) - migrate the outgoing SQL 2008R2 Instance and all databases to the new server running 2022, the old SSRS 2008 server will continue to work when pointed to this server.

Phase 2. (to be done a few weeks later) migrate the SSRS instance to a new server running SSRS 2022. This is the bit which I need to do more investigation into and may need assistance on, primarily whether a 2022 SSRS instance can simply be pointed to a ReportServer database that was previously created by and used by a 2008 version of SSRS ( the Report Server database will be in a SQL 2022 instance)