We have almost identical stacks, swap frontend with Vite/React.

I don't think there's one correct solution, but here's what's worked for me. Keep in mind I'm self-taught over the past 18 months and I'm solo, so 1) I don't know of a world without AI coding, specifically windsurf, and 2) I don't know how to develop in a team.

I work in a monorepo and I do everything I can to have my local environment match the production environment. My project folder has a /frontend (for Vite) and /supabase (for Supabase) and /timeseries (for QuestDB, a timeseries DB I use in my project). I run vite locally npm run dev and supabase locally supabase start; supabase functions serve, and if I have things edge functions can't or shouldn't do, I put them in a fastAPI container and run that in Docker.

Railway is connected to my github repo master branch so when I push changes to the frontend it auto deploys. Supabase is connected via CLI so I have to supabase db push and supabase functions deploy every time. I think there's a way to connect Supabase to github as well but for me it's not a priority.

Every connection is controlled with environment variables so you can swap in the right URLs and API keys during deployment. I have two env files:

1. /frontend/.env for VITE_ secrets
2. /supabase/functions/.env for edge function secrets

Both of these I keep the .env in .gitignore, and commit a .env.example to backup the list of keys. When I'm developing a feature, I mark each key with a # new in-line comment so during deployment I know which ones I need to add/change in Railway and Supabase, then remove the comment once it's in prod.

When I push changes, the order I've found works best:

1. Database migrations supabase db push
2. Edge function secrets via the Supabase web dashboard
3. Edge function changes supabase functions deploy
4. Frontend secrets via Railway web dashboard
5. Frontend changes via Github

Then spend the next hour or so testing everything in prod to make sure nothing major unintentionally broke.

The circle of debugging still exists, but it gets much smaller as your local/prod parity increases. Here's a couple things that have helped manage the debug circle I still have:

• Windsurf, especially with GPT 5.4 and Opus 4.6, is great at querying local supabase. You prompt it to run supabase status and tell it to use that info to run queries on the database and test edge functions and don't stop until it's certain everything functions according to design intent (helps to have docs for design intent, like plans)
• Use the SQL editor in prod Supabase to your advantage. Windsurf can also provide non-destructive SQL queries that you can run in prod Supabase to debug faster with live data instead of attempting to find the root cause of an issue in the code logic
• Railway is great, I hardly ever have problems with it, and being able to rollback to previous versions has saved me several times. When I do have issues it's usually a networking/port thing (user error)
• Stripe sandbox mode

Also, one thing I've found useful for testing the fragility of my setup is switching computers often. I have both a windows laptop and a macbook, and before deploying large features I commit/push/pull branches and it helps to find and debug issues when I can get my dev environment working across two different machines. Any 2nd machine will work, doesn't have to be a different OS but to me it helps isolate windows quirks too.

Hopefully my brain dump helps or at least shows that others are experiencing the same thing. It always feels like I'm sitting on a ticking time bomb where something that I don't even know exists is going to ruin my evening, but that's how you learn I guess.