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Powershell Core - loading assemblies
PowerShell Core is not a "replacement" or "upgrade" for "regular" PowerShell, it's designed to solve different scenarios. None of which have understanding of "UI", apart from the console. Now, afaik the .NET Core folks are actually working on some sort of "port" for the Forms library, but I wouldn't hold my breath (see the announcement here: https://devblogs.microsoft.com/dotnet/net-core-3-and-support-for-windows-desktop-applications/).
In the meantime, for anything that requires even a simple UI-based prompt, keep using good old Windows PowerShell.
spongyrynoMicrosoft
If PowerShell Core is not a replacement for Windows PowerShell, then why is there no longer any ongoing development or maintenance on Windows PowerShell, with 100% of the PowerShell team working exclusively on PowerShell Core?
That's a question you should be asking the relevant folks at Microsoft. It was a poor judgement on their end, one that will finally be addressed with the release of v7. You can read the announcement blog for more details: https://devblogs.microsoft.com/powershell/the-next-release-of-powershell-powershell-7/