diff --git a/subprojects/robotpy-wpilib/gen/Alert.yml b/subprojects/robotpy-wpilib/gen/Alert.yml
index 1abf25776..1047429de 100644
--- a/subprojects/robotpy-wpilib/gen/Alert.yml
+++ b/subprojects/robotpy-wpilib/gen/Alert.yml
@@ -18,3 +18,15 @@ classes:
       SetText:
       GetText:
       GetType:
+    inline_code: |
+      .def("close", [](frc::Alert &self) {
+        py::gil_scoped_release release;
+        self.Set(false);
+      }, py::doc("Disables the alert"))
+      .def("__enter__", [](frc::Alert &self) -> frc::Alert& {
+        return self;
+      })
+      .def("__exit__", [](frc::Alert &self, py::args args) {
+        py::gil_scoped_release release;
+        self.Set(false);
+      })
diff --git a/subprojects/robotpy-wpilib/tests/conftest.py b/subprojects/robotpy-wpilib/tests/conftest.py
index 1a926f3ac..88728aa91 100644
--- a/subprojects/robotpy-wpilib/tests/conftest.py
+++ b/subprojects/robotpy-wpilib/tests/conftest.py
@@ -3,6 +3,7 @@
 import pytest
 import ntcore
 import wpilib
+from wpilib.simulation._simulation import _resetWpilibSimulationData
 
 
 @pytest.fixture
@@ -11,7 +12,15 @@ def cfg_logging(caplog):
 
 
 @pytest.fixture(scope="function")
-def nt(cfg_logging):
+def wpilib_state():
+    try:
+        yield None
+    finally:
+        _resetWpilibSimulationData()
+
+
+@pytest.fixture(scope="function")
+def nt(cfg_logging, wpilib_state):
     instance = ntcore.NetworkTableInstance.getDefault()
     instance.startLocal()
 
@@ -20,4 +29,3 @@ def nt(cfg_logging):
     finally:
         instance.stopLocal()
         instance._reset()
-        wpilib._wpilib._clearSmartDashboardData()
diff --git a/subprojects/robotpy-wpilib/tests/test_alert.py b/subprojects/robotpy-wpilib/tests/test_alert.py
new file mode 100644
index 000000000..ceecc3d87
--- /dev/null
+++ b/subprojects/robotpy-wpilib/tests/test_alert.py
@@ -0,0 +1,223 @@
+import typing as T
+
+import pytest
+
+from ntcore import NetworkTableInstance
+from wpilib import Alert, SmartDashboard
+from wpilib.simulation import pauseTiming, resumeTiming, stepTiming
+
+AlertType = Alert.AlertType
+
+
+@pytest.fixture(scope="function")
+def group_name(nt, request):
+
+    group_name = f"AlertTest_{request.node.name}"
+    yield group_name
+
+    SmartDashboard.updateValues()
+    assert len(get_active_alerts(nt, group_name, AlertType.kError)) == 0
+    assert len(get_active_alerts(nt, group_name, AlertType.kWarning)) == 0
+    assert len(get_active_alerts(nt, group_name, AlertType.kInfo)) == 0
+
+
+def get_subscriber_for_type(
+    nt: NetworkTableInstance, group_name: str, alert_type: AlertType
+):
+    subtable_name = {
+        AlertType.kError: "errors",
+        AlertType.kWarning: "warnings",
+        AlertType.kInfo: "infos",
+    }.get(alert_type, "unknown")
+    topic = f"/SmartDashboard/{group_name}/{subtable_name}"
+    return nt.getStringArrayTopic(topic).subscribe([])
+
+
+def get_active_alerts(
+    nt: NetworkTableInstance, group_name: str, alert_type: AlertType
+) -> T.List[str]:
+    SmartDashboard.updateValues()
+    with get_subscriber_for_type(nt, group_name, alert_type) as sub:
+        return sub.get()
+
+
+def is_alert_active(
+    nt: NetworkTableInstance, group_name: str, text: str, alert_type: AlertType
+):
+    active_alerts = get_active_alerts(nt, group_name, alert_type)
+    return text in active_alerts
+
+
+def assert_state(
+    nt: NetworkTableInstance,
+    group_name: str,
+    alert_type: AlertType,
+    expected_state: T.List[str],
+):
+    assert expected_state == get_active_alerts(nt, group_name, alert_type)
+
+
+def test_set_unset_single(nt, group_name):
+    with Alert(group_name, "one", AlertType.kError) as one:
+
+        assert not is_alert_active(nt, group_name, "one", AlertType.kError)
+        assert not is_alert_active(nt, group_name, "two", AlertType.kInfo)
+
+        one.set(True)
+        assert is_alert_active(nt, group_name, "one", AlertType.kError)
+
+        one.set(True)
+        assert is_alert_active(nt, group_name, "one", AlertType.kError)
+
+        one.set(False)
+        assert not is_alert_active(nt, group_name, "one", AlertType.kError)
+
+
+def test_set_unset_multiple(nt, group_name):
+    with (
+        Alert(group_name, "one", AlertType.kError) as one,
+        Alert(group_name, "two", AlertType.kInfo) as two,
+    ):
+
+        assert not is_alert_active(nt, group_name, "one", AlertType.kError)
+        assert not is_alert_active(nt, group_name, "two", AlertType.kInfo)
+
+        one.set(True)
+        assert is_alert_active(nt, group_name, "one", AlertType.kError)
+        assert not is_alert_active(nt, group_name, "two", AlertType.kInfo)
+
+        one.set(True)
+        two.set(True)
+        assert is_alert_active(nt, group_name, "one", AlertType.kError)
+        assert is_alert_active(nt, group_name, "two", AlertType.kInfo)
+
+        one.set(False)
+        assert not is_alert_active(nt, group_name, "one", AlertType.kError)
+        assert is_alert_active(nt, group_name, "two", AlertType.kInfo)
+
+
+def test_set_is_idempotent(nt, group_name):
+    group_name = group_name
+    with (
+        Alert(group_name, "A", AlertType.kInfo) as a,
+        Alert(group_name, "B", AlertType.kInfo) as b,
+        Alert(group_name, "C", AlertType.kInfo) as c,
+    ):
+
+        a.set(True)
+        b.set(True)
+        c.set(True)
+
+        start_state = get_active_alerts(nt, group_name, AlertType.kInfo)
+        assert set(start_state) == {"A", "B", "C"}
+
+        b.set(True)
+        assert_state(nt, group_name, AlertType.kInfo, start_state)
+
+        a.set(True)
+        assert_state(nt, group_name, AlertType.kInfo, start_state)
+
+
+def test_close_unsets_alert(nt, group_name):
+    group_name = group_name
+    with Alert(group_name, "alert", AlertType.kWarning) as alert:
+        alert.set(True)
+        assert is_alert_active(nt, group_name, "alert", AlertType.kWarning)
+    assert not is_alert_active(nt, group_name, "alert", AlertType.kWarning)
+
+
+def test_set_text_while_unset(nt, group_name):
+    group_name = group_name
+    with Alert(group_name, "BEFORE", AlertType.kInfo) as alert:
+        assert alert.getText() == "BEFORE"
+        alert.set(True)
+        assert is_alert_active(nt, group_name, "BEFORE", AlertType.kInfo)
+        alert.set(False)
+        assert not is_alert_active(nt, group_name, "BEFORE", AlertType.kInfo)
+        alert.setText("AFTER")
+        assert alert.getText() == "AFTER"
+        alert.set(True)
+        assert not is_alert_active(nt, group_name, "BEFORE", AlertType.kInfo)
+        assert is_alert_active(nt, group_name, "AFTER", AlertType.kInfo)
+
+
+def test_set_text_while_set(nt, group_name):
+    with Alert(group_name, "BEFORE", AlertType.kInfo) as alert:
+        assert alert.getText() == "BEFORE"
+        alert.set(True)
+        assert is_alert_active(nt, group_name, "BEFORE", AlertType.kInfo)
+        alert.setText("AFTER")
+        assert alert.getText() == "AFTER"
+        assert not is_alert_active(nt, group_name, "BEFORE", AlertType.kInfo)
+        assert is_alert_active(nt, group_name, "AFTER", AlertType.kInfo)
+
+
+def test_set_text_does_not_affect_sort(nt, group_name):
+    pauseTiming()
+    try:
+        with (
+            Alert(group_name, "A", AlertType.kInfo) as a,
+            Alert(group_name, "B", AlertType.kInfo) as b,
+            Alert(group_name, "C", AlertType.kInfo) as c,
+        ):
+
+            a.set(True)
+            stepTiming(1)
+            b.set(True)
+            stepTiming(1)
+            c.set(True)
+
+            expected_state = get_active_alerts(nt, group_name, AlertType.kInfo)
+            expected_state[expected_state.index("B")] = "AFTER"
+
+            b.setText("AFTER")
+            assert_state(nt, group_name, AlertType.kInfo, expected_state)
+    finally:
+        resumeTiming()
+
+
+def test_sort_order(nt, group_name):
+    pauseTiming()
+    try:
+        with (
+            Alert(group_name, "A", AlertType.kInfo) as a,
+            Alert(group_name, "B", AlertType.kInfo) as b,
+            Alert(group_name, "C", AlertType.kInfo) as c,
+        ):
+
+            a.set(True)
+            assert_state(nt, group_name, AlertType.kInfo, ["A"])
+
+            stepTiming(1)
+            b.set(True)
+            assert_state(nt, group_name, AlertType.kInfo, ["B", "A"])
+
+            stepTiming(1)
+            c.set(True)
+            assert_state(nt, group_name, AlertType.kInfo, ["C", "B", "A"])
+
+            stepTiming(1)
+            c.set(False)
+            assert_state(nt, group_name, AlertType.kInfo, ["B", "A"])
+
+            stepTiming(1)
+            c.set(True)
+            assert_state(nt, group_name, AlertType.kInfo, ["C", "B", "A"])
+
+            stepTiming(1)
+            a.set(False)
+            assert_state(nt, group_name, AlertType.kInfo, ["C", "B"])
+
+            stepTiming(1)
+            b.set(False)
+            assert_state(nt, group_name, AlertType.kInfo, ["C"])
+
+            stepTiming(1)
+            b.set(True)
+            assert_state(nt, group_name, AlertType.kInfo, ["B", "C"])
+
+            stepTiming(1)
+            a.set(True)
+            assert_state(nt, group_name, AlertType.kInfo, ["A", "B", "C"])
+    finally:
+        resumeTiming()