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Might have been a timing issue. Here's how i resolved it using a reverse connection (https://devblogs.microsoft.com/python/python-in-visual-studio-code-july-2020-release/):

.vscode/launch.json

{
  "version": "0.2.0",
  "configurations": [
    {
      "name": "Python: Attach using listen",
      "type": "python",
      "request": "attach",
      "listen": {
        "host": "127.0.0.1",
        "port": 5678
      }
    }
  ]
}

and in `___main___.py`:

import debugpy
debugpy.connect(('localhost', 5678))

With this method, you start the debugger before running

pulumi up

.