diff --git a/.github/workflows/e2e.yml b/.github/workflows/e2e.yml
index d8aa9ec7d7..2ec5ac470b 100644
--- a/.github/workflows/e2e.yml
+++ b/.github/workflows/e2e.yml
@@ -42,6 +42,8 @@ jobs:
       - name: 📥 Download deps
         run: pnpm install --frozen-lockfile --filter trigger.dev...
 
+      # Prisma clients generate concurrently and share one engine binary in the
+      # pnpm store; the generate script retries the transient Windows EPERM race.
       - name: 📀 Generate Prisma Client
         run: pnpm run generate
 
diff --git a/internal-packages/database/package.json b/internal-packages/database/package.json
index ec0bc950b8..560cf229dd 100644
--- a/internal-packages/database/package.json
+++ b/internal-packages/database/package.json
@@ -15,7 +15,7 @@
   },
   "scripts": {
     "clean": "rimraf dist",
-    "generate": "prisma generate",
+    "generate": "node ../../scripts/retry-prisma-generate.mjs",
     "db:migrate:dev:create": "prisma migrate dev --create-only",
     "db:migrate:deploy": "prisma migrate deploy",
     "db:push": "prisma db push",
diff --git a/internal-packages/run-ops-database/package.json b/internal-packages/run-ops-database/package.json
index cbeb0279b0..7bfe0fe271 100644
--- a/internal-packages/run-ops-database/package.json
+++ b/internal-packages/run-ops-database/package.json
@@ -25,7 +25,7 @@
   },
   "scripts": {
     "clean": "rimraf dist",
-    "generate": "prisma generate",
+    "generate": "node ../../scripts/retry-prisma-generate.mjs",
     "db:migrate:dev:create": "prisma migrate dev --create-only",
     "db:migrate:deploy": "node scripts/migrate.mjs deploy",
     "db:migrate:status": "node scripts/migrate.mjs status",
diff --git a/scripts/retry-prisma-generate.mjs b/scripts/retry-prisma-generate.mjs
new file mode 100644
index 0000000000..f20fa4616c
--- /dev/null
+++ b/scripts/retry-prisma-generate.mjs
@@ -0,0 +1,53 @@
+// Retry wrapper around `prisma generate`. Our two prisma clients pin the same
+// prisma version and so share one package instance in the pnpm store; when
+// `turbo run generate` runs them concurrently both race to write the shared
+// query-engine binary, and on Windows the loser fails with `EPERM ... rename`.
+// Retrying lets it succeed once the engine file is present and unlocked. On
+// non-Windows the first attempt succeeds, so this is a zero-cost no-op.
+import { spawnSync } from "node:child_process";
+
+const MAX_ATTEMPTS = 5;
+const BASE_DELAY_MS = 500;
+
+// Transient, retryable filesystem contention on the shared engine binary.
+const TRANSIENT =
+  /\b(EPERM|EBUSY|EACCES)\b|operation not permitted|resource busy or locked|being used by another process/i;
+
+const passthroughArgs = process.argv.slice(2);
+
+function sleepSync(ms) {
+  Atomics.wait(new Int32Array(new SharedArrayBuffer(4)), 0, 0, ms);
+}
+
+let lastStatus = 1;
+
+for (let attempt = 1; attempt <= MAX_ATTEMPTS; attempt++) {
+  const result = spawnSync("prisma", ["generate", ...passthroughArgs], {
+    shell: true,
+    encoding: "utf8",
+  });
+
+  process.stdout.write(result.stdout ?? "");
+  process.stderr.write(result.stderr ?? "");
+
+  if (result.status === 0) {
+    process.exit(0);
+  }
+
+  lastStatus = result.status ?? 1;
+
+  const output = `${result.stdout ?? ""}${result.stderr ?? ""}`;
+  const isRetryable = TRANSIENT.test(output);
+
+  if (!isRetryable || attempt === MAX_ATTEMPTS) {
+    break;
+  }
+
+  const delay = BASE_DELAY_MS * attempt;
+  console.error(
+    `prisma generate hit a transient filesystem error (attempt ${attempt}/${MAX_ATTEMPTS}); retrying in ${delay}ms...`
+  );
+  sleepSync(delay);
+}
+
+process.exit(lastStatus);