What will it take to support evaluating in the context of the library of the currently open file

That's actually what we do :) The comment above didn't mention it, but we pass through the active file in the context (it's non-standard, but all we have for now):

Dart-Code/src/extension/providers/debug_adapter_global_evaluation_context_factory.ts

Lines 34 to 39 in 7389b2c

    
           if (message.command === "evaluate" && message.arguments?.context === "repl") { 
        
           	const doc = getActiveRealFileEditor()?.document; 
        
           	if (doc && isDartDocument(doc)) { 
        
           		message.arguments.context = doc?.uri.toString(); 
        
           	} 
        
           }

And then in the debug adapter, we read this and find the relevant library for that script:

https://github.com/dart-lang/sdk/blob/80a6670d5d081bf6542036979791a8f666adfc1d/pkg/dds/lib/src/dap/adapters/dart.dart#L975

There's no UI to allow you to select, it just uses the current file. We could change this, although I don't know how nice the UI would be - but you can always open a specific file if you want to use that library.

What we don't support though is a way to choose the isolate.

	if (message.command === "evaluate" && message.arguments?.context === "repl") {
	const doc = getActiveRealFileEditor()?.document;
	if (doc && isDartDocument(doc)) {
	message.arguments.context = doc?.uri.toString();
	}
	}

Support global evaluation in SDK DAPs #4636

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