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couple things:

I can only run the pulumi runtime via pulumi pre to trigger the code above and see the output because the entry point is always index.ts.

You can use automation API to trigger deployments, but they invoke the pulumi CLI, yes

Thanks @billowy-army-68599 for the pointer. I will have to check out automations API to see if it's useful. Here's a more recent manifest of an error that I wish there's a better way to debug

Diagnostics:
  pulumi:pulumi:Stack (demo)
    error: Running program '...' failed with an unhandled exception:
SyntaxError: Unexpected identifier

ooh yeah that doesn’t look fun. Is there a repro?

I'm sure it's some typescript error or some misconfigured env. The point of that was to show that it's hard to do debugging when the only entry point available is through pulumi CLI. Because then it makes it difficult to debug something that is just typescript itself. Hence the original question of whether it's possible to add breakpoints.

This blog post covers how to achieve that in .NET and Visual Studio. I realise that’s not your stack, but it might offer some inspiration. Can you add a

debugger

statement somewhere in your program?