diff --git a/furtka/gateway.py b/furtka/gateway.py
index 067c449..e9f778d 100644
--- a/furtka/gateway.py
+++ b/furtka/gateway.py
@@ -214,13 +214,27 @@ def run_connect(gateway_url: str, registration_token: str, box_name: str) -> Non
     systemd-run from `POST /api/gateway/connect`), writing state
     transitions as it goes so the UI can poll instead of the request
     thread blocking on a slow/unreachable gateway.
+
+    A registration saved by an earlier attempt whose tunnel failed to come
+    up is reused rather than registering again — re-registering would leave
+    the first box (and its wg-easy peer) orphaned on the gateway.
     """
-    write_state("registering")
-    try:
-        config = register(gateway_url, registration_token, box_name)
-    except GatewayError as e:
-        write_state("error", error=str(e))
-        return
+    existing = load_config()
+    if existing is not None:
+        if existing["gateway_url"] != gateway_url.rstrip("/"):
+            write_state(
+                "error",
+                error=f"already registered with {existing['gateway_url']} — disconnect first",
+            )
+            return
+        config = existing
+    else:
+        write_state("registering")
+        try:
+            config = register(gateway_url, registration_token, box_name)
+        except GatewayError as e:
+            write_state("error", error=str(e))
+            return
 
     write_state("starting_tunnel")
     try:
diff --git a/tests/test_gateway.py b/tests/test_gateway.py
index 89fd279..a7888c6 100644
--- a/tests/test_gateway.py
+++ b/tests/test_gateway.py
@@ -280,6 +280,58 @@ def test_run_connect_tunnel_failure_writes_error_state(gw, monkeypatch):
     assert gw.load_config()["box_id"] == "abc"
 
 
+def test_run_connect_retry_after_tunnel_failure_reuses_registration(gw, monkeypatch):
+    register_calls = []
+
+    def urlopen(req, timeout):
+        register_calls.append(req.full_url)
+        return _FakeResp({"box_id": "abc", "box_token": "abc.x", "wg": WG})
+
+    monkeypatch.setattr("urllib.request.urlopen", urlopen)
+
+    def failing_tunnel(enabled, wg=None):
+        raise gw.wireguard.WireguardError("systemctl failed: unit missing")
+
+    monkeypatch.setattr(gw.wireguard, "set_tunnel_enabled", failing_tunnel)
+    gw.run_connect("https://gw.example.com", "tok", "my-box")
+    assert gw.read_state()["stage"] == "error"
+
+    tunnel_calls = []
+    monkeypatch.setattr(
+        gw.wireguard,
+        "set_tunnel_enabled",
+        lambda enabled, wg=None: tunnel_calls.append((enabled, wg)),
+    )
+    gw.run_connect("https://gw.example.com/", "tok", "my-box")
+
+    # Registered exactly once; the retry only brought the tunnel up.
+    assert register_calls == ["https://gw.example.com/v1/boxes/register"]
+    assert tunnel_calls == [(True, WG)]
+    assert gw.read_state()["stage"] == "done"
+    assert gw.load_config()["box_id"] == "abc"
+
+
+def test_run_connect_refuses_a_different_gateway_while_registered(gw, monkeypatch):
+    monkeypatch.setattr(
+        "urllib.request.urlopen",
+        lambda req, timeout: _FakeResp({"box_id": "abc", "box_token": "abc.x", "wg": WG}),
+    )
+    gw.register("https://gw.example.com", "tok", "box")
+
+    def must_not_call(req, timeout):
+        raise AssertionError("must not register with a second gateway")
+
+    monkeypatch.setattr("urllib.request.urlopen", must_not_call)
+    monkeypatch.setattr(gw.wireguard, "set_tunnel_enabled", lambda enabled, wg=None: None)
+
+    gw.run_connect("https://other.example.com", "tok", "box")
+
+    state = gw.read_state()
+    assert state["stage"] == "error"
+    assert "disconnect first" in state["error"]
+    assert gw.load_config()["gateway_url"] == "https://gw.example.com"
+
+
 def test_deregister_failure_keeps_local_config_for_retry(gw, monkeypatch):
     monkeypatch.setattr(
         "urllib.request.urlopen",