diff --git a/.claude/CLAUDE-KNOWLEDGE.md b/.claude/CLAUDE-KNOWLEDGE.md
index a4013491d..eb14f31c1 100644
--- a/.claude/CLAUDE-KNOWLEDGE.md
+++ b/.claude/CLAUDE-KNOWLEDGE.md
@@ -391,3 +391,6 @@ A: The `/api/v1/internal/metrics` response now intentionally includes `analytics
 
 ## Q: Why can environment config override writes fail with a product/product-line customer type warning after creating a preview project?
 A: The environment override endpoint validates the new environment override against the rendered branch config. Preview dummy payments data must therefore be internally coherent: products assigned to a product line need the same `customerType` as that product line, otherwise unrelated environment patches can fail with warnings like `Product "growth" has customer type "user" but its product line "workspace" has customer type "team"`.
+
+## Q: Why can `pnpm run dev` fail with `ERR_MODULE_NOT_FOUND` for `@stackframe/stack/dist/esm/index.js` during OpenAPI docs generation?
+A: Root `dev` starts the OpenAPI docs watcher at the same time as package `dev` watchers. If a package `dev` script removes `dist` before `tsdown --watch` recreates it, the docs generator can import `apps/backend/src/stack.tsx` while `@stackframe/stack`'s ESM entrypoint is temporarily missing. Package watch scripts should update `dist` in place, and eager generators should wait for package imports to resolve before running.
diff --git a/package.json b/package.json
index bbf30ea56..b1557a610 100644
--- a/package.json
+++ b/package.json
@@ -77,7 +77,7 @@
     "generate-sdks": "pnpm exec tsx ./scripts/generate-sdks.ts",
     "generate-setup-prompt-docs": "pnpm exec tsx ./scripts/generate-setup-prompt-docs.ts",
     "generate-sdks:watch": "chokidar --silent -c 'pnpm run generate-sdks' './packages/template' --ignore './packages/template/package.json' --ignore '**/node_modules/**' --ignore '**/dist/**' --ignore '**/.turbo/**' --throttle 2000",
-    "generate-openapi-docs:watch": "pnpm run --filter=@stackframe/backend codegen-docs && chokidar --silent -c 'pnpm run --filter=@stackframe/backend codegen-docs' './apps/backend/src/app/api/latest/**/route.{js,jsx,ts,tsx}' './apps/backend/src/lib/openapi.ts' './packages/stack-shared/src/interface/webhooks.ts' --throttle 2000",
+    "generate-openapi-docs:watch": "pnpm exec tsx ./scripts/wait-for-dev-package-imports.ts && pnpm run --filter=@stackframe/backend codegen-docs && chokidar --silent -c 'pnpm run --filter=@stackframe/backend codegen-docs' './apps/backend/src/app/api/latest/**/route.{js,jsx,ts,tsx}' './apps/backend/src/lib/openapi.ts' './packages/stack-shared/src/interface/webhooks.ts' --throttle 2000",
     "generate-setup-prompt-docs:watch": "pnpm run generate-setup-prompt-docs && chokidar --silent -c 'pnpm run generate-setup-prompt-docs' './packages/stack-shared/src/ai/prompts.ts' './scripts/generate-setup-prompt-docs.ts' --throttle 2000"
   },
   "devDependencies": {
diff --git a/packages/js/package.json b/packages/js/package.json
index ce7d1cdf4..cbc838838 100644
--- a/packages/js/package.json
+++ b/packages/js/package.json
@@ -41,7 +41,7 @@
     "clean": "rimraf dist && rimraf node_modules",
     "lint": "eslint --ext .tsx,.ts .",
     "build": "rimraf dist && tsdown",
-    "dev": "rimraf dist && tsdown --watch"
+    "dev": "tsdown --watch"
   },
   "files": [
     "README.md",
diff --git a/packages/react/package.json b/packages/react/package.json
index a5cc7fe55..bc702a61a 100644
--- a/packages/react/package.json
+++ b/packages/react/package.json
@@ -41,7 +41,7 @@
     "clean": "rimraf dist && rimraf node_modules",
     "lint": "eslint --ext .tsx,.ts .",
     "build": "rimraf dist && pnpm run css && tsdown",
-    "dev": "rimraf dist && concurrently -n \"build,codegen\" -k \"tsdown --watch\" \"pnpm run codegen:watch\"",
+    "dev": "concurrently -n \"build,codegen\" -k \"tsdown --watch\" \"pnpm run codegen:watch\"",
     "codegen": "pnpm run css",
     "codegen:watch": "pnpm run css:watch",
     "css": "pnpm run css-tw && pnpm run css-sc",
diff --git a/packages/stack/package.json b/packages/stack/package.json
index a8ae93908..4766147f9 100644
--- a/packages/stack/package.json
+++ b/packages/stack/package.json
@@ -41,7 +41,7 @@
     "clean": "rimraf dist && rimraf node_modules",
     "lint": "eslint --ext .tsx,.ts .",
     "build": "rimraf dist && pnpm run css && tsdown",
-    "dev": "rimraf dist && concurrently -n \"build,codegen\" -k \"tsdown --watch\" \"pnpm run codegen:watch\"",
+    "dev": "concurrently -n \"build,codegen\" -k \"tsdown --watch\" \"pnpm run codegen:watch\"",
     "codegen": "pnpm run css",
     "codegen:watch": "pnpm run css:watch",
     "css": "pnpm run css-tw && pnpm run css-sc",
diff --git a/packages/template/package-template.json b/packages/template/package-template.json
index d677db42f..daed224f6 100644
--- a/packages/template/package-template.json
+++ b/packages/template/package-template.json
@@ -53,12 +53,12 @@
 
     "//": "IF_PLATFORM template react-like",
     "build": "rimraf dist && pnpm run css && tsdown",
-    "dev": "rimraf dist && concurrently -n \"build,codegen\" -k \"tsdown --watch\" \"pnpm run codegen:watch\"",
+    "dev": "concurrently -n \"build,codegen\" -k \"tsdown --watch\" \"pnpm run codegen:watch\"",
     "codegen": "pnpm run css",
     "codegen:watch": "pnpm run css:watch"
     ,"//": "ELSE_PLATFORM",
     "build": "rimraf dist && tsdown",
-    "dev": "rimraf dist && tsdown --watch"
+    "dev": "tsdown --watch"
     ,"//": "END_PLATFORM",
 
     "//": "IF_PLATFORM template react-like"
diff --git a/packages/template/package.json b/packages/template/package.json
index e088b299c..f065f2834 100644
--- a/packages/template/package.json
+++ b/packages/template/package.json
@@ -42,7 +42,7 @@
     "clean": "rimraf dist && rimraf node_modules",
     "lint": "eslint --ext .tsx,.ts .",
     "build": "rimraf dist && pnpm run css && tsdown",
-    "dev": "rimraf dist && concurrently -n \"build,codegen\" -k \"tsdown --watch\" \"pnpm run codegen:watch\"",
+    "dev": "concurrently -n \"build,codegen\" -k \"tsdown --watch\" \"pnpm run codegen:watch\"",
     "codegen": "pnpm run css",
     "codegen:watch": "concurrently -n \"css\" -k \"pnpm run css:watch\"",
     "css": "pnpm run css-tw && pnpm run css-sc",
diff --git a/scripts/wait-for-dev-package-imports.ts b/scripts/wait-for-dev-package-imports.ts
new file mode 100644
index 000000000..c9791b6c2
--- /dev/null
+++ b/scripts/wait-for-dev-package-imports.ts
@@ -0,0 +1,118 @@
+import { spawn } from "child_process";
+import path from "path";
+import { setTimeout as sleep } from "timers/promises";
+
+// Root `pnpm run dev` starts eager generators and package watch builds in
+// parallel. `generate-openapi-docs:watch` intentionally runs `codegen-docs`
+// once before starting chokidar, because chokidar only responds to future file
+// changes. Without that initial run, dev docs could serve stale OpenAPI JSON
+// from a previous branch, or no generated JSON at all after a clean checkout,
+// until someone edits an API route.
+//
+// That eager OpenAPI generation imports backend modules, and some of those
+// backend modules resolve workspace packages through their built `dist`
+// entrypoints. Package watch scripts update those entrypoints with
+// `tsdown --watch`, but on a cold checkout, after `pnpm clean`, or during the
+// first package watcher build, the entrypoints may not exist yet even though
+// `tsdown --watch` is about to create them.
+//
+// We keep this wait scoped to the eager generator rather than putting it in
+// front of backend `dev`: the long-running Next dev server can tolerate package
+// watchers warming up, while a one-shot generator exits immediately on a missing
+// import and `concurrently -k` then tears down the whole dev command. Package
+// watch scripts also avoid deleting `dist` in dev mode, which removes the
+// common restart race; this probe covers the remaining cold-start case.
+//
+// This probe waits only for the package imports that the backend-side generator
+// needs. It does not hide real runtime errors: we retry missing-module failures
+// while package builds warm up, and fail immediately for other import failures.
+const repoRoot = path.resolve(__dirname, "..");
+const backendDir = path.join(repoRoot, "apps/backend");
+const timeoutMs = 60_000;
+const retryDelayMs = 1_000;
+
+const probeScript = `
+(async () => {
+  await import('@stackframe/stack');
+  await import('@stackframe/stack-shared/dist/utils/env');
+})().then(
+  () => undefined,
+  (error) => {
+    console.error(error);
+    process.exit(1);
+  },
+);
+`;
+
+type ProbeResult = {
+  exitCode: number | null,
+  output: string,
+};
+
+function runProbe(): Promise<ProbeResult> {
+  return new Promise((resolve, reject) => {
+    const child = spawn("pnpm", ["exec", "tsx", "-e", probeScript], {
+      cwd: backendDir,
+      env: process.env,
+      stdio: ["ignore", "pipe", "pipe"],
+    });
+
+    let output = "";
+
+    child.stdout.setEncoding("utf8");
+    child.stderr.setEncoding("utf8");
+    child.stdout.on("data", (chunk: string) => {
+      output += chunk;
+    });
+    child.stderr.on("data", (chunk: string) => {
+      output += chunk;
+    });
+
+    child.on("error", reject);
+    child.on("close", (exitCode) => {
+      resolve({ exitCode, output });
+    });
+  });
+}
+
+function isMissingModuleError(output: string) {
+  return output.includes("ERR_MODULE_NOT_FOUND") || output.includes("MODULE_NOT_FOUND");
+}
+
+async function main() {
+  const start = performance.now();
+  let lastOutput = "";
+  let hasLoggedWait = false;
+  let isReady = false;
+
+  while (performance.now() - start < timeoutMs) {
+    const result = await runProbe();
+    if (result.exitCode === 0) {
+      isReady = true;
+      break;
+    }
+
+    lastOutput = result.output;
+    if (!isMissingModuleError(result.output)) {
+      throw new Error(`Dev package import probe failed with a non-retryable error:\n${result.output}`);
+    }
+
+    if (!hasLoggedWait) {
+      console.log("Waiting for dev package entrypoints to be generated...");
+      hasLoggedWait = true;
+    }
+    await sleep(retryDelayMs);
+  }
+
+  if (!isReady) {
+    throw new Error(`Timed out waiting for dev package imports to become available. Last probe output:\n${lastOutput}`);
+  }
+}
+
+main().then(
+  () => undefined,
+  (error) => {
+    console.error(error);
+    process.exit(1);
+  },
+);