diff --git a/.cursorrules b/.cursorrules
index 10a164341..f3b356017 100644
--- a/.cursorrules
+++ b/.cursorrules
@@ -328,6 +328,29 @@ npx wrangler deploy
 
 **Important:** Always use `npx wrangler deploy` without any `--env` flags. The deployment uses the default configuration from `wrangler.jsonc` with route `agents.nicholai.work`. Update `wrangler.jsonc` with new env vars in the top-level `vars` section.
 
+### Deployment Checklist (must be followed exactly):
+
+1. **Never use npm.** Always run commands with pnpm (e.g. `pnpm install`, `pnpm dev`, `pnpm build`).
+
+2. **Before every deploy, run the Cloudflare build step:**
+   ```bash
+   npx @opennextjs/cloudflare build
+   ```
+   If this fails, fix the error before proceeding—Wrangler deploys without this step will push stale assets.
+
+3. **Deploy only after a successful OpenNext build using:**
+   ```bash
+   npx wrangler deploy
+   ```
+   **Do NOT use `--env` flags.** The deployment uses the default configuration from `wrangler.jsonc`.
+
+**Troubleshooting:**
+- "No updated asset files to upload": you skipped the Cloudflare build; rerun step 2.
+- ESLint config errors during build: they're informational—build still succeeds, but you should address them separately.
+- Viewport metadata warning: move viewport values from metadata to generateViewport per Next.js docs.
+
+**No deploy is compliant unless each step above is completed and verified.**
+
 ## Debugging Tips
 
 ### Check Agent Configuration