diff --git a/.env.example b/.env.example
index f069047..10e6d39 100644
--- a/.env.example
+++ b/.env.example
@@ -172,10 +172,14 @@ ENGRAPHIS_DECAY_HALFLIFE_DAYS=7
 # ENGRAPHIS_SMTP_PASSWORD=
 #
 # ── Client side (end-user machines) ─────────────────────────────────────────
-# Optional license-server override. When unset, clients use the URL signed into the key,
-# then the built-in managed relay. Paid Pro/Team keys always require a renewable lease.
-# ENGRAPHIS_CLOUD_URL=https://<your-vendor-host>
-
-# Vendor/fulfillment server only: URL signed into newly minted keys. When unset, issued
-# keys use ENGRAPHIS_RELAY_URL (the built-in managed relay by default).
-# ENGRAPHIS_KEY_CLOUD_URL=https://your-license-server.example.com
+# Paid keys require a revocable, machine-bound lease from the managed service. The
+# built-in default is https://team.engraphis.com; override only for a different vendor
+# deployment. Free-tier use remains local and does not require the service.
+# ENGRAPHIS_CLOUD_URL=https://team.engraphis.com
+
+# Server-side license enforcement (vendor/fulfillment server only): when set, every key
+# minted by the Polar webhook carries a signed enforce:"cloud" claim + this URL, and the
+# client requires a live lease from it (revocable, seat-counted, useless offline).
+# Set this to the canonical managed-service URL for newly issued keys. Older keys carrying
+# the retired Railway hostname are migrated by the client without changing their signature.
+# ENGRAPHIS_KEY_CLOUD_URL=https://team.engraphis.com
diff --git a/CHANGELOG.md b/CHANGELOG.md
index 79fe34b..409adc9 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -5,6 +5,15 @@ All notable changes to Engraphis are documented here. Format loosely follows
 
 ## [Unreleased]
 
+### Fixed
+- Existing paid keys signed before the managed-service domain migration now route the
+  retired Railway license host to `https://team.engraphis.com`; new defaults use the
+  canonical domain for license leases and managed sync. License, trial, and invite
+  requests now send an explicit Engraphis User-Agent so Cloudflare does not reject
+  Python's default `urllib` signature with error 1010. A configured key that falls back
+  to free during an outage now retries automatically, including from the dashboard's
+  background refresh loop, so service recovery no longer requires a restart or re-entry.
+
 ### Added
 - **Agent Connect for hosted Team instances.** Members can mint SHA-256-hashed per-user
   bearer tokens in Settings and use the hosted v2 store through `POST /api/remember`,
diff --git a/README.md b/README.md
index ca79e75..5b63dd7 100644
--- a/README.md
+++ b/README.md
@@ -389,7 +389,7 @@ All via environment (or `.env`):
 | `ENGRAPHIS_LOOP_INTERVAL` | `60` | Background consolidation loop interval in seconds (0 = disabled) |
 | `ENGRAPHIS_DECAY_HALFLIFE_DAYS` | `7` | Ebbinghaus decay half-life (higher = memories persist longer) |
 | `ENGRAPHIS_FORWARDED_ALLOW_IPS` | `127.0.0.1` | Trusted reverse-proxy IPs for TLS termination (`*` = trust all) |
-| `ENGRAPHIS_RELAY_URL` | built-in | Managed sync relay URL (Pro/Team) |
+| `ENGRAPHIS_RELAY_URL` | `https://team.engraphis.com` | Managed sync relay URL (Pro/Team) |
 | `ENGRAPHIS_AUTOSYNC_LOOP` | `1` | Kill switch for the in-process auto-sync loop (0 = off) |
 
 See `.env.example` for the full list including commercial/vendor, email delivery, and
diff --git a/tests/test_cloud_license.py b/tests/test_cloud_license.py
index d73f130..967ede4 100644
--- a/tests/test_cloud_license.py
+++ b/tests/test_cloud_license.py
@@ -17,7 +17,7 @@
 from fastapi.testclient import TestClient
 
 from engraphis import cloud_license, licensing
-from engraphis.config import settings
+from engraphis.config import DEFAULT_RELAY_URL, settings
 from engraphis.inspector import license_cloud
 from engraphis.inspector import license_registry as reg
 from engraphis.licensing import LicenseError, ed25519_public_key, parse_key
@@ -229,6 +229,27 @@ def _urlopen_5xx(req, timeout=None): raise _HTTPError(503)
     assert cloud_license.register("http://cloud.test", _key(), "m-1") is None
 
 
+def test_license_client_sets_cloudflare_safe_headers(monkeypatch):
+    captured = {}
+
+    class _Resp:
+        def read(self): return b'{"lease": null}'
+        def __enter__(self): return self
+        def __exit__(self, *args): return False
+
+    def fake_urlopen(req, timeout=None):
+        captured["user_agent"] = req.get_header("User-agent")
+        captured["accept"] = req.get_header("Accept")
+        return _Resp()
+
+    monkeypatch.setattr(cloud_license.urllib.request, "urlopen", fake_urlopen)
+    assert cloud_license.register("http://cloud.test", _key(), "m-1") is None
+    assert captured == {
+        "user_agent": "Engraphis/1.0 (+https://engraphis.com)",
+        "accept": "application/json",
+    }
+
+
 def test_revalidate_revoked_deletes_lease(monkeypatch):
     # A paid key with a valid local lease is periodically checked online. Background
     # revalidation uses the same denial path and deletes the lease immediately.
@@ -626,6 +647,26 @@ def fake_register(base, k, mid, **kw):
     assert got.plan == "pro" and got.has("sync")
 
 
+def test_retired_baked_in_url_migrates_to_current_relay(monkeypatch):
+    """Existing signed keys must survive the vendor's Railway-to-domain migration."""
+    key = _enforced_key(cloud_url="https://engraphis-production.up.railway.app")
+    lic_parsed = parse_key(key)
+    calls = {}
+
+    def fake_register(base, k, mid, **kw):
+        calls["base"] = base
+        payload = {"v": 1, "key_id": lic_parsed.key_id, "plan": lic_parsed.plan,
+                   "features": sorted(lic_parsed.features), "machine_id": mid,
+                   "issued": int(time.time()), "expires": int(time.time() + 3600)}
+        return cloud_license.compose_lease(payload, SECRET)
+
+    monkeypatch.setattr(cloud_license, "register", fake_register)
+    monkeypatch.setenv("ENGRAPHIS_LICENSE_KEY", key)
+    got = licensing.current_license(refresh=True)
+    assert calls["base"] == DEFAULT_RELAY_URL == "https://team.engraphis.com"
+    assert got.plan == "pro" and got.has("sync")
+
+
 def test_all_paid_keys_require_server_even_without_enforce_claim(monkeypatch):
     """Online-only (closes the offline-key bypass): even a key WITHOUT the enforce claim
     (old "offline" style) must obtain a live lease. Server unreachable → fail closed;
@@ -645,6 +686,26 @@ def ok_register(base, k, mid, **kw):
     assert got.plan == "pro" and got.has("sync")
 
 
+def test_configured_key_retries_after_free_fallback_cache(monkeypatch):
+    """A transient outage must not pin a valid configured key to free forever."""
+    key = _key()
+    lic_parsed = parse_key(key)
+    monkeypatch.setenv("ENGRAPHIS_LICENSE_KEY", key)
+    monkeypatch.setattr(cloud_license, "register", lambda *a, **k: None)
+    assert licensing.current_license(refresh=True).plan == "free"
+    assert licensing._cache_recheck_at != float("inf")
+
+    def ok_register(base, k, mid, **kw):
+        payload = {"v": 1, "key_id": lic_parsed.key_id, "plan": lic_parsed.plan,
+                   "features": sorted(lic_parsed.features), "machine_id": mid,
+                   "issued": int(time.time()), "expires": int(time.time() + 3600)}
+        return cloud_license.compose_lease(payload, SECRET)
+
+    monkeypatch.setattr(cloud_license, "register", ok_register)
+    monkeypatch.setattr(licensing, "_cache_recheck_at", 0)
+    assert licensing.current_license().plan == "pro"
+
+
 # ── team-invite relay: self-hosted dashboards with no mail account of their own ────────
 # borrow the vendor's, gated by a real 'team' key (same trust boundary as every other
 # licensed feature) and rate-limited per key so it can't become an open relay.
diff --git a/tests/test_config.py b/tests/test_config.py
index f78ab77..a5e080b 100644
--- a/tests/test_config.py
+++ b/tests/test_config.py
@@ -9,6 +9,9 @@
 from engraphis.config import Settings
 
 
+RETIRED_RELAY_URL = "https://engraphis-production.up.railway.app"
+
+
 def test_rerank_model_defaults_to_empty(monkeypatch):
     monkeypatch.delenv("ENGRAPHIS_RERANK_MODEL", raising=False)
     assert Settings().rerank_model == ""
@@ -62,3 +65,17 @@ def test_license_server_url_migrates_retired_signed_host(monkeypatch):
     assert config.resolve_license_server_url(
         "https://engraphis-production.up.railway.app/",
     ) == config.DEFAULT_RELAY_URL
+
+
+def test_retired_cloud_url_override_is_canonicalized(monkeypatch):
+    monkeypatch.setenv("ENGRAPHIS_CLOUD_URL", RETIRED_RELAY_URL + "/")
+    assert (
+        config.resolve_license_server_url("https://signed.example")
+        == config.DEFAULT_RELAY_URL
+    )
+
+
+def test_retired_relay_url_override_is_canonicalized(monkeypatch):
+    monkeypatch.delenv("ENGRAPHIS_CLOUD_URL", raising=False)
+    monkeypatch.setattr(config.settings, "relay_url", RETIRED_RELAY_URL)
+    assert config.resolve_license_server_url() == config.DEFAULT_RELAY_URL
diff --git a/tests/test_dashboard_v2.py b/tests/test_dashboard_v2.py
index ff5334c..3b5f45e 100644
--- a/tests/test_dashboard_v2.py
+++ b/tests/test_dashboard_v2.py
@@ -76,6 +76,17 @@ def test_team_mode_env_opt_out_parsing(monkeypatch, raw):
     assert _enabled() is False
 
 
+def test_license_background_refresh_retries_configured_key(monkeypatch):
+    from engraphis.dashboard_app import _refresh_configured_license
+
+    calls = []
+    monkeypatch.setattr(lic, "_read_key_material", lambda: "configured-key")
+    monkeypatch.setattr(
+        lic, "current_license", lambda *, refresh=False: calls.append(refresh))
+    _refresh_configured_license()
+    assert calls == [True]
+
+
 def test_team_setup_waits_for_active_license(monkeypatch, tmp_path):
     with _client(monkeypatch, tmp_path, team=True, key=None) as c:
         state = c.get("/api/auth/state").json()