@egamma Would using the TSS_DEBUG environment variable work for this situation? Here's a launch config I prototyped for writing a vscode extension that loads a tsserver plugin:

{
    "version": "0.1.0",
    "configurations": [
        {
            "name": "Launch Extension",
            "type": "extensionHost",
            "request": "launch",
            "runtimeExecutable": "${execPath}",
            "args": ["--extensionDevelopmentPath=${workspaceRoot}" ],
            "env": {
                "TSS_DEBUG": "9000"
            },
            "stopOnEntry": false,
            "sourceMaps": true,
            "preLaunchTask": "npm"
        }, {
            "type": "node",
            "request": "attach",
            "name": "Attach to TSServer",
            "port": 9000
        }
    ],
    "compounds": [
        {
            "name": "Compound",
            "configurations": ["Launch Extension", "Attach to TSServer"]
        }
    ]
}

This compound debug config isn't perfect since the tsserver doesn't actually startup until the TS extension is activated, but it should give you a consistent port to targeted

Investigate improving the development support for TS server plugins #26235

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