Hi,
I setup a demo project here.
The command now dev --debug run correctly, but when I request the url, the builder seems to be stuck and no error is shown.
➜ zeit-now-bug-winston git:(master) now dev --debug
> [debug] [2019-09-05T11:40:25.850Z] Found config in file /zeit-now-bug-winston/now.json
> [debug] [2019-09-05T11:40:25.854Z] Using Now CLI 16.1.3
> [debug] [2019-09-05T11:40:25.857Z] user supplied known subcommand
> Now CLI 16.1.3 dev (beta) — https://zeit.co/feedback/dev
> [debug] [2019-09-05T11:40:26.010Z] The yarn executable is already cached, not re-downloading
> [debug] [2019-09-05T11:40:26.015Z] Reading `package.json` file
> [debug] [2019-09-05T11:40:26.015Z] Reading `now.json` file
> [debug] [2019-09-05T11:40:26.025Z] Locating files /zeit-now-bug-winston
> [debug] [2019-09-05T11:40:26.026Z] Ignoring /zeit-now-bug-winston/.git
> [debug] [2019-09-05T11:40:26.027Z] Ignoring /zeit-now-bug-winston/.gitignore
> [debug] [2019-09-05T11:40:26.028Z] Ignoring /zeit-now-bug-winston/node_modules
> [debug] [2019-09-05T11:40:26.029Z] Locating files /zeit-now-bug-winston: 3.823ms
> [debug] [2019-09-05T11:40:26.041Z] No builders need to be installed
> [debug] [2019-09-05T11:40:26.197Z] Adding build match for "index.js"
> [debug] [2019-09-05T11:40:26.228Z] Got listen error: EADDRINUSE
> NOTE: Requested port 3000 is already in use
> Ready! Available at http://localhost:3001
> GET /
> [debug] [2019-09-05T11:40:28.003Z] Using cached `now.json` config
> [debug] [2019-09-05T11:40:28.011Z] Using cached `now.json` config
> [debug] [2019-09-05T11:40:28.011Z] Building asset "index.js-index.js" for "GET /"
> Building @now/node:index.js
> [debug] [2019-09-05T11:40:28.014Z] Using `@now/[email protected]`
> [debug] [2019-09-05T11:40:28.014Z] Creating build process for index.js
downloading user files...
download complete [0ms]
installing dependencies for user's code...
missing `engines` in `package.json`, using default range: 8.10.x
installing to /zeit-now-bug-winston
yarn install v1.17.3
warning package.json: No license field
warning No license field
[1/4] Resolving packages...
success Already up-to-date.
Done in 0.13s.
install complete [502ms]
running user script...
script complete [1ms]
tracing input files...
> [debug] [2019-09-05T11:40:33.775Z] No builders were updated
Thanks for reporting this. We'll take a look!
Hey there @davidbillamboz. Sorry for the late reply. Are you still having this issue? Your example repo works correctly for me when I try it:

Node version: v12.15.0
Now CLI version: v17.1.2-canary.6
Closing for inactivity. Let us know if you want this re-opened.
Most helpful comment
Thanks for reporting this. We'll take a look!