diff --git a/CHANGELOG.md b/CHANGELOG.md
index 3737b80e..d7330bd7 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -1,5 +1,11 @@
 # Change Log
 
+## [Unreleased]
+
+### Fixed
+
+- Fix `dumps()` and `item()` rendering a `datetime` whose UTC offset is not a whole number of minutes (e.g. the historical LMT offsets `zoneinfo` yields, such as `+00:19:32`) or a tz-aware `time` as invalid TOML that no parser, including tomlkit's own, accepts; both now raise `ValueError` instead. The same check covers `DateTime.astimezone()`/`replace()` and `Time.replace()`, which build a new item from the result.
+
 ## [0.15.1] - 2026-07-17
 
 ### Changed
diff --git a/tests/test_items.py b/tests/test_items.py
index e331caeb..45009acf 100644
--- a/tests/test_items.py
+++ b/tests/test_items.py
@@ -20,6 +20,7 @@
 from tests.util import assert_is_ppo
 from tests.util import elementary_test
 from tomlkit import api
+from tomlkit import dumps
 from tomlkit import parse
 from tomlkit.container import OutOfOrderTableProxy
 from tomlkit.exceptions import NonExistentKey
@@ -726,6 +727,58 @@ def test_datetimes_behave_like_datetimes(tz_utc: tzinfo, tz_pst: tzinfo) -> None
     assert doc.as_string() == "dt = 2018-07-23T12:34:56-05:00"
 
 
+def test_datetime_with_sub_minute_utc_offset_is_rejected() -> None:
+    # TOML offset date-times are RFC 3339: the offset is always HH:MM, so an
+    # offset with seconds (e.g. the LMT offsets zoneinfo yields for historical
+    # dates, Europe/Amsterdam before 1937 is +00:19:32) cannot be written.
+    # It used to be rendered verbatim, producing a document that no TOML
+    # parser, including tomlkit's own, would accept.
+    amsterdam_lmt = timezone(timedelta(minutes=19, seconds=32))
+    dt = datetime(1930, 1, 1, 12, 0, tzinfo=amsterdam_lmt)
+
+    with pytest.raises(ValueError, match="whole number of minutes"):
+        item(dt)
+
+    with pytest.raises(ValueError, match="whole number of minutes"):
+        dumps({"dt": dt})
+
+    with pytest.raises(ValueError, match="whole number of minutes"):
+        item(datetime(2020, 1, 1, tzinfo=timezone(timedelta(microseconds=1))))
+
+    # The same offsets can be reached from a valid item through the datetime
+    # API, so those paths must refuse as well instead of rendering garbage.
+    i = item(datetime(2020, 1, 1, 12, 0, tzinfo=timezone.utc))
+    with pytest.raises(ValueError, match="whole number of minutes"):
+        i.astimezone(amsterdam_lmt)
+    with pytest.raises(ValueError, match="whole number of minutes"):
+        i.replace(tzinfo=amsterdam_lmt)
+
+    # Whole-minute offsets keep working exactly as before.
+    i = item(
+        datetime(2020, 1, 1, 12, 0, tzinfo=timezone(timedelta(hours=5, minutes=30)))
+    )
+    assert i.as_string() == "2020-01-01T12:00:00+05:30"
+    assert i.astimezone(timezone.utc).as_string() == "2020-01-01T06:30:00+00:00"
+
+
+def test_time_with_utc_offset_is_rejected() -> None:
+    # TOML local times carry no offset at all; a tz-aware time used to be
+    # rendered as e.g. `01:02:03+00:00`, which no TOML parser accepts.
+    t = time(1, 2, 3, tzinfo=timezone.utc)
+
+    with pytest.raises(ValueError, match="cannot have a UTC offset"):
+        item(t)
+
+    with pytest.raises(ValueError, match="cannot have a UTC offset"):
+        dumps({"t": t})
+
+    i = item(time(1, 2, 3))
+    with pytest.raises(ValueError, match="cannot have a UTC offset"):
+        i.replace(tzinfo=timezone.utc)
+
+    assert i.replace(hour=4).as_string() == "04:02:03"
+
+
 def test_dates_behave_like_dates() -> None:
     i = item(date(2018, 7, 22))
 
diff --git a/tomlkit/items.py b/tomlkit/items.py
index 31369b03..36739cef 100644
--- a/tomlkit/items.py
+++ b/tomlkit/items.py
@@ -49,6 +49,29 @@ def __call__(self, __value: Any, /) -> Item: ...
 AT = TypeVar("AT", bound="AbstractTable")
 
 
+def _check_datetime_offset(value: datetime) -> None:
+    """Refuse a UTC offset that TOML cannot write.
+
+    TOML offset date-times follow RFC 3339, whose offset is always ``HH:MM``.
+    Python allows offsets with seconds and microseconds (``zoneinfo`` yields
+    them for historical dates, e.g. Europe/Amsterdam before 1937 is
+    ``+00:19:32``), and ``isoformat()`` renders them, producing a document
+    that no TOML parser accepts. Raise instead of writing an invalid file.
+    """
+    offset = value.utcoffset()
+    if offset is not None and (offset.seconds % 60 or offset.microseconds):
+        raise ValueError(
+            f"TOML cannot represent a UTC offset of {offset}: "
+            "it must be a whole number of minutes"
+        )
+
+
+def _check_time_offset(value: time) -> None:
+    """Refuse a tz-aware time: TOML local times carry no offset at all."""
+    if value.utcoffset() is not None:
+        raise ValueError("TOML local times cannot have a UTC offset")
+
+
 @overload
 def item(value: bool, _parent: Item | None = ..., _sort_keys: bool = ...) -> Bool: ...  # type: ignore[overload-overlap]
 
@@ -1070,6 +1093,7 @@ def __init__(
     ) -> None:
         super().__init__(trivia or Trivia())
 
+        _check_datetime_offset(self)
         self._raw = raw or self.isoformat()
 
     def unwrap(self) -> datetime:
@@ -1291,6 +1315,7 @@ def __init__(
     ) -> None:
         super().__init__(trivia or Trivia())
 
+        _check_time_offset(self)
         self._raw = raw
 
     def unwrap(self) -> time: