Visual Studio Code

Create a new Node.js debug configuration, add -r ts-node/register to node args and move the program to the args list (so VS Code doesn't look for outFiles).

{
    "configurations": [{
        "type": "node",
        "request": "launch",
        "name": "Launch Program",
        "runtimeArgs": [
            "-r",
            "ts-node/register"
        ],
        "args": [
            "${workspaceFolder}/src/index.ts"
        ]
    }],
}

Note: If you are using the --project <tsconfig.json> command line argument as per the Configuration Options, and want to apply this same behavior when launching in VS Code, add an "env" key into the launch configuration: "env": { "TS_NODE_PROJECT": "<tsconfig.json>" }.