diff --git a/tests/test_api_client/test_serializer.py b/tests/test_api_client/test_serializer.py
index b190bf15..fbb9b3b4 100644
--- a/tests/test_api_client/test_serializer.py
+++ b/tests/test_api_client/test_serializer.py
@@ -306,6 +306,7 @@ def test_serialize_datetime(value, expected):
     "value,expected",
     [
         (datetime.fromtimestamp(0.0), "/Date(0)/"),
+        (datetime(1960, 1, 1, tzinfo=tz.UTC), "/Date(-315619200000+0000)/"),
         (datetime.fromtimestamp(1439424000.0), "/Date(1439424000000)/"),
         (datetime.fromtimestamp(1439434356.790), "/Date(1439434356790)/"),
         (datetime(2015, 8, 13, tzinfo=tz.UTC), "/Date(1439424000000+0000)/"),
@@ -337,6 +338,35 @@ def test_serialize_datetime_ms(value, expected):
     assert result == expected
 
 
+def test_serialize_naive_pre_epoch_datetime_ms_uses_local_timezone():
+    value = datetime(1960, 1, 1, 12, 30)
+    windows_local = getattr(tz, "tzwinlocal", None)
+    local_tz = windows_local() if windows_local is not None else tz.tzlocal()
+    local_offset = local_tz.utcoffset(value) or timedelta()
+    utc_value = (value - local_offset).replace(tzinfo=tz.UTC)
+    epoch = datetime(1970, 1, 1, tzinfo=tz.UTC)
+    expected_ms = int((utc_value - epoch).total_seconds() * 1000)
+
+    assert serialize_datetime_ms(value) == "/Date({})/".format(expected_ms)
+
+
+@pytest.mark.parametrize(
+    "value",
+    [
+        datetime(1971, 1, 1, 12, 30),
+        datetime(2015, 8, 13, 12, 30),
+        datetime(2024, 4, 7, 2, 30, fold=0),
+        datetime(2024, 4, 7, 2, 30, fold=1),
+        datetime(2024, 10, 6, 2, 30, fold=0),
+        datetime(2024, 10, 6, 2, 30, fold=1),
+    ],
+)
+def test_serialize_naive_datetime_ms_preserves_platform_timestamp_semantics(value):
+    expected_ms = int(value.timestamp() * 1000)
+
+    assert serialize_datetime_ms(value) == "/Date({})/".format(expected_ms)
+
+
 # serialize_date_ms tests
 @pytest.mark.parametrize(
     "value,expected",
@@ -356,6 +386,15 @@ def test_serialize_date_ms(value, expected):
     assert result == expected
 
 
+def test_serialize_pre_epoch_date_ms_uses_utc_midnight():
+    value = date(1960, 1, 1)
+    utc_value = datetime.combine(value, datetime.min.time()).replace(tzinfo=tz.UTC)
+    epoch = datetime(1970, 1, 1, tzinfo=tz.UTC)
+    expected_ms = int((utc_value - epoch).total_seconds() * 1000)
+
+    assert serialize_date_ms(value) == "/Date({})/".format(expected_ms)
+
+
 # serialize_base_model tests
 def test_serialize_base_model():
     # given test model
diff --git a/xero_python/api_client/serializer.py b/xero_python/api_client/serializer.py
index cf508da9..83e3012a 100644
--- a/xero_python/api_client/serializer.py
+++ b/xero_python/api_client/serializer.py
@@ -12,6 +12,27 @@
 DICT_DATA_TYPE = re.compile(r"^dict(?:\[(.*)\])?$")
 LIST_DATA_TYPE = re.compile(r"^list(?:\[(.*)\])?$")
 TUPLE_DATA_TYPE = re.compile(r"^tuple(?:\[(.*)\])?$")
+UNIX_EPOCH = datetime(1970, 1, 1, tzinfo=tz.UTC)
+
+
+def local_timezone():
+    """Return a local timezone that supports pre-epoch dates on Windows."""
+    windows_local = getattr(tz, "tzwinlocal", None)
+    if windows_local is not None:
+        return windows_local()
+    return tz.tzlocal()
+
+
+def datetime_timestamp(value):
+    """Return seconds from the Unix epoch without platform timestamp limits."""
+    try:
+        # Preserve the platform's existing naive-local DST and fold semantics.
+        return value.timestamp()
+    except (OSError, OverflowError):
+        pass
+    if value.tzinfo is None:
+        value = value.replace(tzinfo=local_timezone())
+    return (value.astimezone(tz.UTC) - UNIX_EPOCH).total_seconds()
 
 
 def data_type(value, explicit_type=None):
@@ -159,7 +180,7 @@ def serialize_datetime_ms(value, explicit_type=None):
     :return: serialized object
     """
     tz_str = value.strftime("%z")
-    timestamp_s = value.timestamp()
+    timestamp_s = datetime_timestamp(value)
     timestamp_ms = int(timestamp_s * 1000)
     return "/Date({}{})/".format(timestamp_ms, tz_str)
 
@@ -180,7 +201,7 @@ def serialize_date_ms(value, explicit_type=None):
     else:
         raise ValueError("Can't serialize {!r} into Microsoft date json format")
 
-    timestamp_s = datetime_value.timestamp()
+    timestamp_s = datetime_timestamp(datetime_value)
     timestamp_ms = int(timestamp_s * 1000)
     return "/Date({})/".format(timestamp_ms)