Requirements to Get SQL Server 2008 Working

[EncodedBird]

I know everyone who isn't stuck with SQL server 2008 for some arcane reason will hate reading this, but you can get it to work in azure data studio. Here are the requirements:

1. You must have the absolute newest patch level available to the general public. This means you are running Microsoft SQL Server 2008 R2 (SP3-GDR) (KB4057113) - 10.50.6560.0 (there is an extended support patch that is newer but we don't require that). Currently if you have updated to SP3 (a manual update) then pulled in the patches windows update will provide, you can then get KB4057113.
2. You must have a certificate installed. A self-signed one will do, although note that if you use "trust server certificate" you are defeating the intent of this requirement. This was painful, but I was able to accomplish this by:
   A: Generating the cert with openssl (comes as part of git) on the host machine. You can look up instructions to make self-signed cert then convert to pfx. I read somewhere that it needs to be at least 4096 bits for some things to support it, but I forgot where.
   B: Import the converted pfx into a newer version of windows, then export it from the keystore with the older algorithm (so not sha-256). The resulting pfx is importable into the old windows version your sql server is likely coupled with (server 2012 in my case). This stackoverflow post is extremely helpful here.
   C: You must then go into the registry and enable TLS1.2 per Microsoft's Instructions

SQL 2008 will never get TLS1.3 or higher, so eventually once these step fails it will be permanently obsolete I am sure.