I have a local SQL server database with Always Encrypted columns, and a master key stored in Azure Key Vault. I can easily perform CRUD operations with a .Net web application but I have a requirement to modify (insert/update) data via powershell. I have spent a number of days investigating this but I can’t get it working. There are a couple of SO posts from a few years ago (Unable to insert into an always encrypted table using PowerShell and Updating T-SQL always encrypted column with PowerShell), but I haven’t been to get updates/inserts working with AKV.