diff --git a/.env.example b/.env.example
index da8dd4d..cd00e17 100644
--- a/.env.example
+++ b/.env.example
@@ -16,6 +16,10 @@ OIDC_CLIENT_ID=
 OIDC_CLIENT_SECRET=
 OIDC_DISCOVERY_URL=https://auth.bosslevel.dev/.well-known/openid-configuration
 
+# Ory Network project slug or UUID (`ory list projects`). When set with
+# OIDC_CLIENT_ID, `pnpm dev` registers the portless callback via the ory CLI.
+# ORY_PROJECT_ID=confident-sinoussi-hk8lp01xr9
+
 # Optional: refuse script runs without a session once login works
 # AUTH_REQUIRED=true
 
diff --git a/package.json b/package.json
index d0241ef..d45958b 100644
--- a/package.json
+++ b/package.json
@@ -4,7 +4,7 @@
   "type": "module",
   "packageManager": "pnpm@11.10.0",
   "scripts": {
-    "dev": "node scripts/dev.mjs",
+    "dev": "node --env-file-if-exists=.env scripts/dev.mjs",
     "dev:ports": "turbo run dev",
     "build": "turbo run build",
     "start": "turbo run start",
diff --git a/scripts/dev.mjs b/scripts/dev.mjs
index 28f0fc6..45897e2 100644
--- a/scripts/dev.mjs
+++ b/scripts/dev.mjs
@@ -4,7 +4,11 @@
 //
 // The API is not in this list: the frontend serves @repo/api at /api/* from its
 // own process. `pnpm --filter @repo/backend serve:portless` runs it standalone.
+//
+// When ORY_PROJECT_ID + OIDC_CLIENT_ID are set, registers this worktree's OIDC
+// callback on the Ory client before servers start (see ory-redirect.mjs).
 import { spawn } from "node:child_process"
+import { ensureOryRedirectUri } from "./ory-redirect.mjs"
 import { portlessName } from "./portless-name.mjs"
 
 const APPS = [["frontend", "returntypes"]]
@@ -14,6 +18,14 @@ for (const [label, app] of APPS) {
   console.log(`  ${label.padEnd(9)} ${url}`)
   console.log(`  ${"api".padEnd(9)} ${url}/api  (${url}/api/scalar)`)
 }
+
+if (process.env.ORY_PROJECT_ID && process.env.OIDC_CLIENT_ID) {
+  ensureOryRedirectUri()
+} else if (process.env.OIDC_CLIENT_ID && !process.env.ORY_PROJECT_ID) {
+  console.log(
+    `  ory      skip redirect sync (set ORY_PROJECT_ID to register the portless callback)`
+  )
+}
 console.log()
 
 const child = spawn("pnpm", ["exec", "turbo", "run", "dev:portless"], {
diff --git a/scripts/ory-redirect.mjs b/scripts/ory-redirect.mjs
new file mode 100644
index 0000000..70ad92e
--- /dev/null
+++ b/scripts/ory-redirect.mjs
@@ -0,0 +1,148 @@
+// Registers this worktree's portless OIDC callback on the Ory OAuth2 client so
+// login works without hand-editing redirect URIs for every branch.
+//
+// Requires ORY_PROJECT_ID (Ory Network project slug or UUID) and OIDC_CLIENT_ID.
+// No-ops when either is unset, or when the `ory` CLI is missing / unauthenticated.
+import { spawnSync } from "node:child_process"
+import { mkdtempSync, rmSync, writeFileSync } from "node:fs"
+import { tmpdir } from "node:os"
+import { join } from "node:path"
+import { portlessName } from "./portless-name.mjs"
+
+const CALLBACK_PATH = "/api/auth/oauth2/callback/oidc"
+
+/** Fields Hydra rejects or ignores on replace — strip before --file update. */
+const READ_ONLY = new Set([
+  "AdditionalProperties",
+  "created_at",
+  "updated_at",
+  "client_secret_expires_at",
+])
+
+function warn(msg) {
+  console.warn(`  ory: ${msg}`)
+}
+
+function ory(args, { quiet = false } = {}) {
+  const result = spawnSync("ory", args, {
+    encoding: "utf8",
+    stdio: ["ignore", "pipe", "pipe"],
+  })
+  if (result.error) {
+    if (result.error.code === "ENOENT") {
+      return {
+        ok: false,
+        error: "ory CLI not found — install it or skip ORY_PROJECT_ID",
+      }
+    }
+    return { ok: false, error: result.error.message }
+  }
+  if (result.status !== 0) {
+    const err = (
+      result.stderr ||
+      result.stdout ||
+      `ory exited ${result.status}`
+    ).trim()
+    return { ok: false, error: quiet ? err.split("\n")[0] : err }
+  }
+  return { ok: true, stdout: result.stdout }
+}
+
+export function redirectUriForFrontend() {
+  return `https://${portlessName("returntypes")}.localhost${CALLBACK_PATH}`
+}
+
+/**
+ * Ensure `redirectUri` is on the OAuth2 client. Returns true when the client
+ * already had it or the update succeeded.
+ */
+export function ensureOryRedirectUri({
+  projectId = process.env.ORY_PROJECT_ID,
+  clientId = process.env.OIDC_CLIENT_ID,
+  redirectUri = redirectUriForFrontend(),
+} = {}) {
+  if (!(projectId && clientId)) return false
+
+  const got = ory(
+    [
+      "get",
+      "oauth2-client",
+      clientId,
+      "--project",
+      projectId,
+      "--format",
+      "json",
+    ],
+    { quiet: true }
+  )
+  if (!got.ok) {
+    warn(`could not read client: ${got.error}`)
+    return false
+  }
+
+  let client
+  try {
+    client = JSON.parse(got.stdout)
+  } catch {
+    warn("could not parse ory get oauth2-client output")
+    return false
+  }
+
+  const existing = Array.isArray(client.redirect_uris)
+    ? client.redirect_uris
+    : []
+  if (existing.includes(redirectUri)) {
+    console.log(`  ory      redirect URI already registered`)
+    console.log(`           ${redirectUri}`)
+    return true
+  }
+
+  const next = {
+    ...Object.fromEntries(
+      Object.entries(client).filter(([k]) => !READ_ONLY.has(k))
+    ),
+    redirect_uris: [...existing, redirectUri],
+  }
+  // Prefer env secret so a replace cannot blank the stored one.
+  if (process.env.OIDC_CLIENT_SECRET) {
+    next.client_secret = process.env.OIDC_CLIENT_SECRET
+  }
+
+  const dir = mkdtempSync(join(tmpdir(), "ory-redirect-"))
+  const file = join(dir, "client.json")
+  try {
+    writeFileSync(file, `${JSON.stringify(next, null, 2)}\n`)
+    const updated = ory(
+      [
+        "update",
+        "oauth2-client",
+        clientId,
+        "--project",
+        projectId,
+        "--file",
+        file,
+        "--format",
+        "json",
+        "-y",
+      ],
+      { quiet: true }
+    )
+    if (!updated.ok) {
+      warn(`could not update client: ${updated.error}`)
+      return false
+    }
+  } finally {
+    rmSync(dir, { recursive: true, force: true })
+  }
+
+  console.log(`  ory      registered redirect URI`)
+  console.log(`           ${redirectUri}`)
+  return true
+}
+
+if (import.meta.filename === process.argv[1]) {
+  const ok = ensureOryRedirectUri()
+  process.exit(
+    ok || !(process.env.ORY_PROJECT_ID && process.env.OIDC_CLIENT_ID) ? 0 : 1
+  )
+}
diff --git a/turbo.json b/turbo.json
index 814af4d..acd4c90 100644
--- a/turbo.json
+++ b/turbo.json
@@ -1,6 +1,11 @@
 {
   "$schema": "https://turbo.build/schema.json",
   "ui": "tui",
+  "globalPassThroughEnv": [
+    "ORY_PROJECT_ID",
+    "OIDC_CLIENT_ID",
+    "OIDC_CLIENT_SECRET"
+  ],
   "tasks": {
     "build": {
       "dependsOn": ["^build"],