I attempted to deploy the JSON.NET assembly into the CLR a few years ago. Unfortunately, at the time anyway, I had to set the assembly permission to UNSAFE before before SQL Server accepted it. This was in no way acceptable and so I abandoned the effort. Did you find this was required as well?

Having failed to deploy JSON.NET with SAGE permissions, I resumed developing my own library I named J-SQL. After reading Phil Factors T-SQL implementation I was able to finally get past parsing more than a generation deep in a nested hierarchy. So, for those who care, anyone is free to use my solution available at https://github.com/jgcoding/J-SQL.git.

Be sure the JSON string is compressed as I am still working out addressing tab, line-feeds, carriage returns, and spaces not residing within a properly quoted string value as one may see when the JSON string is formatted for display.

I should have this worked out soon.

Enjoy

John Galt Coding