diff --git a/doc/source/whatsnew/v2.2.0.rst b/doc/source/whatsnew/v2.2.0.rst
index 29a2d5c0b5877..e40553353fc20 100644
--- a/doc/source/whatsnew/v2.2.0.rst
+++ b/doc/source/whatsnew/v2.2.0.rst
@@ -349,6 +349,7 @@ I/O
 - Bug in :func:`read_excel`, with ``engine="xlrd"`` (``xls`` files) erroring when file contains NaNs/Infs (:issue:`54564`)
 - Bug in :func:`to_excel`, with ``OdsWriter`` (``ods`` files) writing boolean/string value (:issue:`54994`)
 - Bug in :meth:`pandas.read_excel` with an ODS file without cached formatted cell for float values (:issue:`55219`)
+- Bug where :meth:`DataFrame.to_json` would raise an ``OverflowError`` instead of a ``TypeError`` with unsupported NumPy types (:issue:`55403`)
 
 Period
 ^^^^^^
diff --git a/pandas/_libs/src/vendored/ujson/python/objToJSON.c b/pandas/_libs/src/vendored/ujson/python/objToJSON.c
index 8c55505f61b51..a4c93f1560a0e 100644
--- a/pandas/_libs/src/vendored/ujson/python/objToJSON.c
+++ b/pandas/_libs/src/vendored/ujson/python/objToJSON.c
@@ -1610,9 +1610,9 @@ void Object_beginTypeContext(JSOBJ _obj, JSONTypeContext *tc) {
                                   PyArray_DescrFromType(NPY_DOUBLE));
         tc->type = JT_DOUBLE;
         return;
-    } else if (PyArray_Check(obj) && PyArray_CheckScalar(obj)) {
+    } else if (PyArray_CheckScalar(obj)) {
         PyErr_Format(PyExc_TypeError,
-                     "%R (0d array) is not JSON serializable at the moment",
+                     "%R (numpy-scalar) is not JSON serializable at the moment",
                      obj);
         goto INVALID;
     } else if (object_is_na_type(obj)) {
diff --git a/pandas/tests/io/json/test_ujson.py b/pandas/tests/io/json/test_ujson.py
index d5f8c5200c4a3..646f6745936bd 100644
--- a/pandas/tests/io/json/test_ujson.py
+++ b/pandas/tests/io/json/test_ujson.py
@@ -814,10 +814,19 @@ def test_array_float(self):
 
     def test_0d_array(self):
         # gh-18878
-        msg = re.escape("array(1) (0d array) is not JSON serializable at the moment")
+        msg = re.escape(
+            "array(1) (numpy-scalar) is not JSON serializable at the moment"
+        )
         with pytest.raises(TypeError, match=msg):
             ujson.ujson_dumps(np.array(1))
 
+    def test_array_long_double(self):
+        msg = re.compile(
+            "1234.5.* \\(numpy-scalar\\) is not JSON serializable at the moment"
+        )
+        with pytest.raises(TypeError, match=msg):
+            ujson.ujson_dumps(np.longdouble(1234.5))
+
 
 class TestPandasJSONTests:
     def test_dataframe(self, orient):